Crossdressing, sending pictures, masturbation, getting caught, punishment, caging, desperation, degradation, milking


Owen stood in front of the mirror, staring at himself. He was wearing a pink crop top and a black skirt, the pleats swirling around his hips with every shift of his weight. He ran his hands over his body gently, loving the way he looked. Jester bought it for him a while ago and made him wear it, and since then, he would put it on every once in a while when he had the house to himself. He knew they wouldn't be home until late that night, and he decided that he would spend his spare time doing whatever the hell he wanted. They weren't there to stop him.

He knelt in front of the mirror and leaned back, sitting on his heels. He gently stoked himself and his heart started racing. He sped up and threw his head back, moaning loudly. They would be so upset with him if they saw him right now. If they came home early and caught him touching himself in a skirt.

"Ffffuck." He muttered to himself, thinking about what they would do to him if they found him. Probably bend him over and spank him. Or whip him with the belt until his ass was covered in bruises. His mouth started watering, and drool dripped down his chin. They would probably make him spread his legs, and put on a strap on that was too big for him and fuck him until he was gaping.

He wanted them to find him.

He grabbed his phone and opened the camera. He pulled the skirt back and spread his legs, showing off his swollen dick. He stuck his tongue out and snapped a picture, sending it to Jester.

Within minutes he heard the front door slam and their footsteps as they ran up the stairs. He stood and put his hands behind his back, grinning wide.

"Hi Jes." He said, swaying his hips. They looked at him and frowned.

"Take it off."

"I thought you liked it when I wore this, master." Owen said teasingly.

"Take. It. Off. Now, kitten." Owen stripped hurriedly, heart pounding. Once his clothes were in a pile at his feet, Jester pointed to the bathroom door. "Go take a cold shower. As cold as you can stand." Owen froze.

"W-what?" Jester scowled and stepped forward.

"NOW." Owen's breath hitched and he turned, rushing to the bathroom.

He turned on the shower and stepped in. Cold water cascaded down his body and he had to bite his cheek to keep from shouting. His body tightened, the shock of the cold almost burning his skin.

"Don't get out until I say so." Jester said. "Do you understand?"

"Yes." He heard them step out of the bathroom and close the door behind them.


After about 15 minutes of near torture, Owen heard the bathroom door open. Jester sat on the counter across from the shower.

"You are going to wear something for me. I am going to put it on, and you are not going to talk back. If you talk back or disobey me, you are going to keep it on for another hour. Do you understand me?" Owen shivered.

"Yes." Owen said, voice shaking.

"You may get out." Owen shut off the water, relieved. He pushed the curtain aside and stepped out, shivering. Jester was standing in front of him, still angry. They got on their knees and slid a cold metal cage around his now soft dick. Owen's breath hitched, and he winced, the feeling of cold metal and their warm hands against his sensitive skin making him whimper. They gently locked it and stood, putting the key in their pocket. "How does it feel?"

"Weird."

"Not uncomfortable?" Owen shook his head. "Good." Jester turned and walked out of the bathroom, beckoning him to follow.

He stood in the middle of the bedroom, body still dripping wet. He was shivering as he watched Jester slowly undress. Jester pulled on a strap, swaying their hips slightly once it was on. Owen's mouth watered as he thought about how it would feel inside of him. They pulled on a pair of lacy thigh highs and a lacy bra, making sure to do it slow so Owen could watch. He felt his dick throb against the cold metal, but it stayed soft in the restraints.

Once they were dressed, they turned and pointed to the shirt and skirt, still lying on the floor.

"Put them back on, kitten." Owen bent over and picked them up, slowly pulling them on. Once they were on, he turned back around and put his hands behind his back.

"Put your hands on the bed and spread your legs." Owen obeyed, sticking his ass out for them. They squirted some lube onto their fingers and rubbed gentle circles around his asshole. He whimpered and leaned back, desperate to be filled. They slid two fingers in and Owen moaned, his asshole tightening around their fingers.

Wet noises filled the room as they fingered him, lube dripping down his ass. Their fingers would occasionally slide over his prostate, sending shocks of pleasure up his spine. They added another finger and smiled, admiring how his asshole stretched around them.

"Look how wet your little pussy is for me." Jester said. "So eager to be filled." Owen whimpered.

"Yes, master. For-aahn! Just for you!"

"Do you want that, kitten?" They said, pulling their fingers out. "Do you want me to fuck your tight little girl hole?"

"Yes! Yes master, please!" Owen cried, gripping the sheets.

They grabbed a bottle of lube and squirted some into their hand, stroking the toy hanging between their legs slowly. They spit on his ass and Owen whimpered as it dripped over his asshole. They pressed the head of the toy against it and pushed, gently sliding it in. Owen arched his back and moaned, his legs trembling. They filled him slowly, with painfully long thrusts, inch by inch until Owen felt like he was going to lose his mind if they didn't speed up.

They pushed the toy against his prostate and he whimpered. An almost-pain swelled between his legs, as blood filled his balls but had nowhere to go, his little cock still restrained by the cage. The dull ache made his head swim, and he was having trouble holding himself up. Jester held his hips and started to speed up, the sound of their hips slapping against his ass filling the room.

"How does it feel, kitten?" Jester said, dragging their nails down his thighs.

"G-good!" Owen cried, arms shaking.

"You like it when I fuck your pretty little cunt?"

"Fffuuuck! Yes, master!" They thrust into him as hard as they could, ramming their cock into his prostate. Owen's vision swam and his arms collapsed beneath him. He pressed his face into the mattress, his ass still in the air. He gripped the sheets and Moaned as they abused his asshole, the overwhelming throbbing between his legs making him dizzy. Jester reached between his legs and swiped their thumb across the tip of his dick poking out of the cage. His hips bucked and he mewled, arching his back.

"I love your soft little cock, kitten." Jester muttered, their breath hos on his back. "How vulnerable and pretty it is." Owen whined, screwing his eyes shut.

"All f-for you" Owen muttered, eyes rolling back. His legs started to tremble, and they had to hold him to keep him from collapsing. Jester slowed their thrusts, making him whine.

"Get on the bed for me." They pulled out, and Owen fell to his knees, gripping the bed with shaking hands. "C'mon, kitten." Owen stood, his knees threatening to buckle. He collapsed onto the bed and spread his legs, looking at Jester pleadingly. They grabbed a pair of cuffs and secured his hands above his head. Then they opened the drawer and pulled out a butt plug, ignoring Owen's protests. They squirted lube on it and stroked it as they climbed on the bed, sitting between his legs.

"I don't want that, I want you, master! Please?" Jester looked down at him angrily.

"Do you remember what I said about talking back?" Owen immediately shut up, nodding his head quickly. "Good girl." They slid the toy into him in one smooth motion, his stretched asshole sucking the toy in. He whined as it filled him, every twitch of his muscles making it shift inside of him. Jester stood and grabbed a remote from the same drawer. "How fast, kitten?" Owen shook his head, eyes wide. "Full speed it is."

Owen tried to protest, but he was cut short by a loud buzzing. He opened his mouth in a silent scream and arched his back. Every muscle in his body tightened as the toy vibrated painfully fast inside of him. He fought against the restraints, desperate to rip off the cage, but the aching between his legs only got worse as Jester stood and watched. They pulled out their phone and smiled.

"Be a good little sissy slut and smile for the camera." They joked, snapping picture after picture. He couldn't keep his hips from bucking as his vision blurred, the toy buzzing overwhelmingly fast. His cock strained against the cage, and his mind swam with desperation. Slobber dripped out of his mouth as he screamed, his eyes rolled back and his tongue hanging out.

Jester sat on the end of the bed and watched, one hand holding up the phone and another between their legs. Wet sounds filled the room as they fingered their dripping pussy, aching for their own release. A long string of almost incomprehensible profanities escaped Owen's lips, his overwhelmed body shaking and trembling, sweat dripping down his legs.

After what felt like eternity, Jester put the phone down and stood.

"Have you had enough, kitten?" Owen couldn't get out the words, so he nodded his head desperately. They slowly turned down the toy, until it was finally still. Owen's breath was ragged, his exhausted body finally stilled as he caught his breath. Jester slid onto the bed and tugged out the toy, making Owen whimper, his voice hoarse. "Do you want me back inside your cute little pussy?" Owen nodded, spreading his legs farther. Jester smiled and put a gentle hand on the inside of his thigh. "You're so needy, kitten." They slid the strap into his asshole easily, and he moaned. "You can't think of anything but finishing now, can you?" Owen shook his head, squeezing his eyes closed as they started fucking his overused asshole. "You just want me to milk your soft little dick, don't you?"

"Mhmm. Y-yes. Please." Owen muttered.

"You want me to milk your tiny little dick while I fuck your sissy asshole?" They dragged their nails down the insides of his thighs.

"ffUCK! YES! Yes, master, please!" Owen screamed, arching his back. Jester grabbed the key from where it was tucked in their bra and unlocked the cage, tossing it aside. They spit on his cock and started stroking it, timing the strokes with their thrusts.

Owen's vision swam and he arched his back, knuckles white around the sheets. He froze for half a second, and then his body shook, his hips bucking as cum spurted out of his cock and all over his chest. His voice broke as he moaned, his chest heaving. Jester kept stroking, only slowing down once his body stilled. They pulled out gently, taking the strap off and putting it aside.

"You're so beautiful, kitten." Jester said as they leaned forward. They gently licked his stomach, cleaning up his cum. He watched them play with it in their mouth and swallow it as they ran their hands over his thighs.

Once they had cleaned him up, they sat next to him and stroked his hair.

"I love you, baby."

"I love you too."