Jesters got a dick now
no this isn't lazy writing, i'm just bored as hell
chastity, caging, desperation, overstimulation, messy sex, overuse, degradation, stepping/crushing
Jester opened the front door and dumped their gym bag on the floor.
"I'm home!" They shouted up the stairs as they walked to the kitchen. Owen came down and stood in the doorway, watching Jester pour themselves water.
"How was your workout?" Owen asked quietly.
"Fine. I'm fucking tired."
"Not too tired?" Owen said, putting his hands behind his back. Jester gulped down their water and looked at him, confused.
"Um, why?"
"It's been a month." Jester blinked and looked at their phone.
"Shit, seriously?" They laughed, putting their cup in the sink and walking over to Owen. "I bet you were counting down the seconds, weren't you?" Owen nodded, looking at the ground at his feet. Jester snapped their fingers. "Look at me when I'm talking to you." Owen stood up straight and looked at them, wide eyed.
"I'm sorry sir." Jester frowned up at him, and Owen's heart raced. Then they smiled and laughed, putting a hand on Owen's arm.
"It's ok, puppy. Don't look so scared." They leaned in and kissed Owen, their post workout musk filling his nose. He whimpered quietly, the smell making his head spin. "C'mon, puppy." Jester cooed, sliding past Owen and walking to the stairs. "Upstairs." Owen followed them eagerly to the bedroom, closing the door behind them.
Owen stood by the door, hands behind his back, shifting his weight from foot to foot nervously while he watched Jester dig through the dresser. Their shirt clung to their body, and Owen could see their dick pressing against their black sweatpants. Jester started to say something, but Owen kept staring at their cock, thinking about how good it felt when they-
"Hey!" Jester snapped their fingers, and Owen jumped. "Are you listening?" Owen nodded hurriedly.
"Yes, yes sir, I am." Jester frowned.
"Don't let me catch you like that again. Now strip." Owen pulled his clothes off quickly, tossing them to the floor in front of the door. Jester smiled, staring between his legs. A small metal cage was wrapped around his soft little cock, a thick ring wrapping around the base of his swollen and aching balls. "It's so cute and small!" Jester cooed, smiling.
"T-thank you sir." Owen said, face flushing.
"Now come here." Jester pointed at the bed and Owen obeyed, sitting against the pillows and spreading his legs. They grabbed his hands and pulled them over his head, tying his wrists tightly to the headboard with rough rope. "Do you want me to put a toy in your cute little ass, or do you want to stay nice and tight for me?" Jester said, looking down at him.
"It's your decision, sir. I'm yours. I do what you want, I'm not in control." They smiled, clearly pleased.
"Good boy!" They said, kissing the top of his head. "That's what I like to hear." They turned and opened a dresser drawer, pulling out a long, curved vibrator with a swollen tip and wide base. Owen shivered as he watched Jester squirt some lube onto the toy and climb onto the bed. They settled between his legs and stroked the vibrator slowly, covering the length of the toy until it was dripping. "Ready, puppy?" Jester asked, smiling.
"Mhm." Owen said, already losing patience. Jester made a pouty face and huffed.
"C'mon, puppy, use your words."
"Yes sir, I'm ready, please just put it in!" Jester raised their eyebrows and smiled.
"Are you really that desperate for this?" They said, pressing the tip of the toy against Owen's twitching asshole.
"Mhm, yes sir." He muttered as he swayed his hips against the toy. Jester pushed, and Owen couldn't keep himself quiet as the toy slowly filled him, stretching his ass until the base was stopping it from going any deeper, and the swollen tip was pushed against his prostate. He arched his back and moaned, grinding his hips against the toy, desperate for friction. Jester put a hand on the inside of his thigh and he stopped, whimpering through gritted teeth. They pressed a button on the base of the toy, and it buzzed to life, vibrating loudly. Owen's body jolted and he moaned loudly, the toy buzzing against his prostate.
"Does that feel good, puppy?" Jester cooed, stroking his caged dick. Owen nodded, unable to get out actual words. "Good. Now," They said, stepping off the bed and standing. "I'm going to shower."
"N-no!" Owen whimpered, fighting against the rope. "Don't gooooo!" Jester watched him struggle, his shaking legs unable to gain traction beneath him.
"You've waited a month, you can wait just a little longer." They said, walking to the bathroom door and closing it behind them.
The shower shut off and Jester stepped out, wrapping a fluffy white towel around their waist. They wrung out their hair and opened the door, steam swirling around their body. As soon as the door opened, they heard Owen whimpering and moaning incoherently from the bed.
"Hi, puppy." They said, walking over and sitting on the bed next to him. His skin was flushed red and slick with sweat, his hair clinging to his forehead. His wrists were raw and red from the rope, every struggle and pull stinging his skin. Drool dripped from his open mouth, whimpers and moans spilling out. There was a sticky mess of cum covering his lap, countless unsatisfying finishes coating his thighs and sticking to the mattress. They slowly ran a hand down his body, stroking his balls as they slid their hand between his legs and turned the vibrator off. Owen's body stopped writhing and he gasped for breath, his legs and arms still trembling.
"N-no fair." Owen muttered, trying to sit up. Jester smiled and stood, walking around the bed to the closet. They bent down and grabbed a pair of pointy toed black heels, slipping them onto their feet.
"I don't have to be fair, puppy, I can do whatever I want to you." They reached over Owen's head and untied the ropes. "C'mon, get up." Owen sat up and slowly stood, his trembling legs threatening to give out beneath him. "Get on your knees, puppy." Owen dropped to his knees harder than he had meant to, and he could feel a bruise spreading almost immediately. Jester tossed their towel aside and grabbed Owen's hair with one hand, using the other to stroke themselves slowly. Owen eagerly opened his mouth and stuck his tongue out before Jester could tell him to. "Aww, are you eager to choke on my cock, puppy?"
"Yes, sir." Owen said, looking up at them with wide eyes. Jester pressed the tip of their dick against his tongue and snapped their hips, shoving it down his throat.
"Such a dirty little slut." Jester growled, ignoring Owen's whimpers of protest as they fucked his throat. Drool dripped onto the floor, lewd wet gurgling noises coming from Owen's throat as he choked on their length. Owen palmed his caged dick while he sucked, his hands shaking. Jester gripped his hair harder and yanked his head back. His eyes rolled back and he gasped for air, whimpering when they twisted a handful of hair. "Are you that fucking desperate?" Jester growled, letting their slobber covered dick brush against his face.
"I-I'm sorry, I-" They stopped him from finishing his sentence by shoving their cock back down his throat, and keeping it there.
"You disgusting little whore." They growled, watching his face flush. His body started to shake, and his eyes filled with tears. He moaned loudly against their dick, grabbing their thighs with shaking hands. Jester pulled back and Owen gasped, chest heaving as he gulped down air. He curled forward and put his head between his knees, head spinning. Jester pressed the heel of their shoe into the back of his head, pushing his face into the carpet. "Get up." They lifted their foot off his head and Owen shakily got to his feet. Jester sat on the bed and grabbed a small key from the bedside table. Owen stepped forward, and they unlocked the cage, roughly tugging it off. "On your knees." Owen stepped back and got to his knees, putting his hands behind his back.
"God, puppy." Jester sighed, looking down at him in disgust. "You're so fucking small." They lifted their foot and dug the toe of their heel into his balls, making him flinch.
"I'm sorry, sir." Owen whimpered.
"I deserve better than this." They ground the flat bottom of their shoe into his cock, crushing it against his body. Owen moaned, and tears filled his eyes. "Someone I can actually feel inside me." They twisted their foot, and Owen yelped. "Someone worth my time." They jabbed the pointy tip into his length, making him cry out and fall back. Jester stood and grabbed his hair, pulling him up and yanking him towards the bed. He collapsed over the side and Jester grabbed his ass, forcing his legs straight. They stroked their dick a few times, Owen's spit still dripping from it. "You're only good for one thing." They pushed the swollen tip of their cock against his asshole and pushed, burying themselves balls deep into his tight little hole.
"Ffuck! Oh my god!" Owen cried, gripping the sheets. His body shook, his hips bucking every time they thrust into his abused prostate.
"I only keep you around for your tight little ass." Jester grunted, heat building in their stomach. "You're my fucking cum slut, and nothing else. There's nothing you're good for, other than holding all my cum."
Their thrusts grew erratic, and they dug their nails into Owen's thighs. Beads of blood popped up around their fingers, and they thrust as deep as they could. Owen could feel their cock twitching inside of him, cum shooting out and filling his insides. His tummy swelled a little as they filled him, ropes of cum spurting out with every little throb.
They ground their hips gently, and without pulling out, they grasped at the bedside table and opened the drawer. They fished out a small butt plug, and spit on it, making it slick. Jester pulled out, and pressed the plug against his ass before any cum could drip out. Owen whimpered and bucked his hips, whimpering when the toy slid past the tight ring of muscle. He was breathing heavily, and his legs were trembling. Jester stepped back and took a breath, watching as Owen stood and collapsed onto the bed, palming his throbbing dick. It was swollen and red, twitching every time his muscles clenched around the plug.
"Sir?" Owen whimpered, sitting up. "C-can I fuck you?" Jester looked at him, eyebrows raised.
"Excuse me?" Jester laughed, and Owen shook his head, eyes wide.
"Please! Please sir, I wanna be inside you, I wanna make you feel good!" Owen said, looking up at them pleadingly. He slid his legs underneath him and put his hands on his knees, his cock poking out from between his legs. Jester sighed, and grabbed their phone, looking at the time.
"Absolutely not." They said, turning away. "You're too small, I'm not wasting my time on that."
"Please, sir. I was good for you all month!" Jester sighed, and nodded.
"Fine." They climbed onto the bed and got on all fours, facing away from Owen. They stuck their butt out and shook it a little, showing themselves off. Owen grabbed a bottle of lube and squirted some onto his dick, making lewd wet noises as he stroked himself. He pushed the tip of his dick against their asshole and pushed, his length sliding in easily. Owen's head swam as he thrust, Jester's ass squeezing around him.
"Y-you feel so good, sir!" Owen moaned, thrusting as fast as he could. His legs were shaking, and he felt pressure building in his stomach. Jester sighed, and reached for the bedside table, grabbing their phone. Owen couldn't see what they were doing, but they weren't paying attention to him. "Sir?" He groaned, voice shaking. "I'm close, I'm really close."
"You better not cum inside, puppy." Jester said, and Owen pulled out, jerking himself off desperately. Jester sat up and turned around, spreading their legs. They reached between their legs and slowly stroked their own cock, making a show of moaning and writing as they did so, how good Owen couldn't make them feel.
"S-sir, I-Mmm!" Owen's hips bucked and cum shot from his cock, splattering against Jester's body. His head swam, and he fell back, holding himself up with one shaking arm as his body trembled and his breath hitched, his spent cock throbbing against the palm of his hand.
Owen collapsed onto his side, breathing heavily. Jester grabbed their towel and wiped the cum off while he caught his breath. He felt light headed, but jumped when he felt Jester grab his ass. They pushed him onto his stomach and forced his legs apart. Owen felt them grip the base of the plug, and is body jolted when they tugged it out. Cum immediately started dripping out, and they wiped it up with their fingers, getting their cock slick with it.
"Sir, I can't, I'm too sensitive!" Owen whimpered, voice hoarse. Jester ignored him, and in one smooth motion, buried their cock into his ass. Owen's back arched and he screamed, stars dancing in his eyes as they abused his prostate. Incoherent protests and profanity spilled from his mouth while they fucked him senseless. Jester moaned, pressure building in their stomach.
"F-fuuuuck." They moaned, their legs starting to tremble. They threw their head back and moaned, their hips bucking as they came. Lights flashed in their eyes and they gripped Owen's hips as they roughly milked themselves with his messy, wet hole. Cum filled Owen's tummy, making it swell as they emptied themselves inside his overused body.
They shakily pulled out and pushed the plug back in, collapsing onto the bed next to Owen.
Once they caught their breath, Jester reached forward and gently stroked his hair out of his face. He smiled and closed his eyes, his breathing slowing.
"I love you." Owen whispered.
"I love you too, baby."