Cross dressing, vibrators, cat ears, daddy/puppy, pegging, anal, cock rings, etc etc
It was raining again. Sheets of rain pounded against the window, nearly drowning out the background buzz of the TV. It was late, later than they should have been up, but Jester sat perched on the overstuffed couch, video game controller clutched in their hand. They had been mining for hours, and their eyes were aching.
"Jes?" Owen called from the doorway. His voice was quiet, softer than usual.
"Yeah?" They grunted, not looking up.
"Um, I found this." He said, and held up a black bag. Jes looked over their shoulder and smiled.
"Oh yeah, I forgot about that. What about it?" The lights were off, the only illumination was the blue glow of the screen, but they could tell his face was flushed red. "Did you look through it?" He nodded. "Well? Do you wanna put it on?"
"I, Um." His heart skipped a few beats as he looked at the contents again. "Yes. Absolutely." Jester smiled.
"Need a hand putting any of it on?"
"Um. No."
"Okay."
"Okay." Owen turned and ran upstairs, closing the bathroom door behind him.
He dumped everything onto the counter and peeled off his shirt. There was a pink crop top, a pink schoolgirl skirt, pink thigh highs, a pair of cat ears, and a box. He changed in seconds, but paused when he got to the box. Jes had to be kidding.
"Done." He muttered as he wandered into the living room. Jester looked over their shoulder and their heart stopped.
"Holy shit, puppy." They couldn't help but stare. The cat ears poked out from his mess of curly brown hair, the tight pink crop top contrasting with his tan skin, The skirt was short, and barely covered his cock, which was forming a tent under the pale fabric.
His face was flushed red and he stared at his hands, which were fidgeting with something small and pink. Jester smiled, holding their hand out. "You figure it out alright?" Owen nodded, and handed them the small controller. They ran their fingers over the sliding switch, and pushed it to the lowest setting. The vibrator he had inside of him started to buzz, and his knees buckled. He had to brace himself on the doorway to keep from falling.
"Fffuck!" He moaned, his legs shaking. They laughed and turned it back down to zero.
"Hoooooly shit, that was the lowest setting baby, you sure you're gonna be alright?" Owen stood back up and nodded.
"Yeah, its just. Uh." Jes raised an eyebrow. "It's right against my. Um. S-spot." Jes grinned, climbing off the couch. They motioned for Owen to come to them, and he did, looking down at them. They grabbed his chin and pulled him closer.
"I'm gonna fucking destroy you, slut." They turned it back on to level one, and he cried out, knees buckling again. This time, he fell to his knees, hands grasping at the skirt. Jes grabbed his throat and squeezed, pulling him in close. His mouth was wide open, eyes half closed. Jes liked up a little drool that had dripped down his chin. "Stand up." They said, voice stern.
Owen did so shakily, the toy audibly vibrating inside of him. They motioned for him to follow them upstairs, and he did, having to nearly drag himself up on the railing. His legs were trembling, but he was getting used to the feeling. It was getting a little more tolerable. He climbed on the bed and sat, watching Jes dig through a dresser drawer. They turned, holding a pair of cuffs in their hand. "You ok with this, puppy?" They asked.
"Fffuck yes." He nodded, and lifted his arms over his head. They wrapped them around his wrists and secured the chin between them to a hook he hadn't realized was on top of the headboard. Jester backed up and their heart fluttered. He was leaning back on the headboard, his arms flexed behind his head, clutching the chains between his wrists. He was squirming, the skirt brushing against his cock every time he moved his legs. he was already close, his cock throbbing with every pulse of the vibrator.
"I got something else I think you'll like." Jester said as they slid off the bed. "Want to watch me put it on?" Owen nodded.
They walked over to the closet, and Owen's heart skipped a beat when they pulled out a Victoria's Secret bag. They slowly peeled off their shirt, but they had their back turned and Owen tried to crane his neck to see. They slid their shorts off, then their underwear. Owen's mouth watered as they bent down to pick up the bag. Their lips were perfect pink and sopping wet. He pulled against the cuffs, wanting nothing but for them to sit on his face.
Hearing him pull on his restraints, Jester turned, smiling.
"You need to be patient, puppy." Owen whimpered.
"I want you to sit on my face, daddy. Please" Jester laughed and turned back around, stepping into a pair of lacy black panties and pulling on thin black bra. They did everything slowly, showing themselves off as they pulled on a leather halter, tightening it around their waist and thighs. "Please." He moaned, tugging on the chain.
Jester reached down and picked up the remote, sliding it up two levels.
"ffuuUUUCK!" Owen arched his back and cried out, every muscle in his body tensing up at once. He fought against the restraints, desperate to touch himself. "Holyshitholyshitholyshit" He whimpered, bucking his hips. His eyes were clenched shut and his vision was white around the edges. He heard Jester giggle, and open another drawer.
"I'm gonna touch you, puppy." They said, putting a gentle hand on his knee. He tried to relax and keep his hips from bucking too violently, but his entire body was shaking. They gently spread his legs and pushed back the skirt, running their hand down his length. He yelped, thrusting his hips, searching for more friction. They pulled their hand away, but he still felt something wrapped around the base.
"W-what did you?" He sputtered. Jester giggled
"Its a cock ring, babe." Owen let out a whimper. "I don't want you coming too soon." They leaned in and kissed him, on all fours over him. When they pulled back, he stared at them, hungrily devouring every little detail. Their crooked smile, their perfect tits, their pink nipples under the lacy, their pussy lips poking out of their lacy crotch less panties, insides of their thighs coated in wet. They reached up and unhooked the chain, letting his hands fall behind his head, still in the cuffs. "Lay down, puppy." Once he was flat on the mattress they climbed over him, gently squeezing his face between their thighs. They smelled fucking amazing. There were two pale, crescent shaped scars on the inside of their thigh from the last time he bit them, and he wanted more than anything to add a matching one on the other leg. He looked up at them pleadingly, and they smiled. "Go ahead, puppy." He scraped his teeth against their cool skin and they whimpered, their dominance wavering. "Fuuuuck, puppy. Please." They muttered, grasping his hair. He slowly sunk his teeth into their leg and they cried out a long string of profanity, pulling grasping his hair painfully tight. His eyes rolled back and he groaned as he licked the wound. Jes was trembling, their legs shaking when he stopped.
"You're so beautiful." He muttered, looking up at them with a crooked smile. Their face flushed bright red.
"Shut up, don't make me gag you." They muttered as they looked away.
"Ooh." Owen said. "Scary." They looked down, frowning.
"Excuse me?" Jester grabbed his face and pulled him in. His face flushed.
"Nothing." They raised an eyebrow. " Nothing, daddy."
"That's what I like to hear, puppy." They said, leaning in for a kiss. Owen sat up and as they kissed Jester shifted their weight over his cock and sat down slowly, groaning as they took his entire length. They rode him for what felt like ours, every thrust of Owen's hips feeling like an electric shock shooting through their veins.
"Fuck daddy, I'm close, I'm really close." Owen mumbled. Jester sped up, the wet sounds of their pussy filling the room. Owen moaned and threw his head back. The toy in his ass and Jester's tight pussy around him felt so fucking good. He felt so close, so fucking close, he needed so desperately to-"ffUCKIGN HELL FUCKFUCKFUUUCK!" He cried, his entire body shaking as Jester slid the controller up to full speed. His eyes were rolled back and his legs were trembling as his vision went white around the edges. He was on the edge, he was so fucking close.
"Does puppy like that?" Jester giggled, still riding him. It felt like he was about to shatter.
"Pleasedaddyletmecumpleasepleaseineeditsobad-" He desperately begged, almost incoherently. Jester grabbed his hair, pulling him close.
"I'll let you cum when you earn it, puppy." They said sternly.
"Please, I can't wait, I need it so bad, please daddy!" He continued to beg, bucking his hips erratically. Jester pinned his hips and slid back, his cock sliding out with a wet pop. "Fuck, daddy, please no don't stop!" Jester stood and grabbed a ball gag from the bedside table, and Owen whimpered.
"You gonna keep begging, or are you going to be good?"
"Please daddy, just let me fucking cum already I-"
They grabbed his face and slid a thumb into his mouth, using it to keep his mouth open. They slid the gag between his teeth and secured it behind his head.
They grabbed the remote and slowly turned it back down to zero. Owen desperately moaned against the gag, almost whining. He was so close.
Jester re-secured the cuffs over his head and knelt back, spreading their legs. As Owen watched, they started touching themselves, slowly. They spread their lips and slid in two fingers, scissoring them inside of themselves. When they pulled them out, they were dripping wet, and they used it like lube, slowly sliding their fingers into Owen. He let out a long soft moan as they pulled out the vibrator.
"I was thinking of using the strap on again, would you like that, puppy?" Owen nodded, whimpering. "Good boy." They got up and put it on, but it was different than the last one they had used. It was bigger, thick enough that they couldn't wrap one hand around it. They used their wet to lube it, moaning quietly as they fingered themselves. "Spread your legs, puppy."
They slid the dildo in and Owen moaned against the gag. He started grinding his hips against it desperately as they began thrusting, getting faster and faster. Jester couldn't help but admire what was in front of them.
Owen was leaning back on the headboard with his hands behind his head, his chest rising and falling with every moan. His face was flushed red and his eyes were rolled back, drool dripping down his chin. His jaw was clenched around the gag and his entire body was shaking.
He started moaning frantically and fighting against the restraints, he was getting close again. His legs were trembling and he felt like he was about to go fucking feral. Jester sped up, and Owen cried out, his back arching as he came all over himself. He struggled to catch his breach, his chest heaving.
Jester pulled the dildo out and Owen whimpered, his legs trembling."You ok puppy?" They asked. Owen smiled.
"Can you do that again?"
