Jesse Discovers Obedience

Jesse stepped into the shower, carrying his dildo. It flopped a little in his hands. He pressed its suction cup base into the shower wall around waist height, and considered it. It was a little larger then his own dick, but still one of the smallest sized realistic options the sex shop had had. It had a nice rubbery material that felt a little like skin if you rubbed it, and replica veins stood out from the shaft.

He'd lubed it up in the sink, and it dripped a little onto the shower floor. Jesse stood back and turned the water on, waiting a moment for it to get hot. He stepped into the water and stood, basking in the soothing warmth. He relaxed, and thought about the porn he'd just been watching. He'd been trying new genres recently, first bisexual and now some outright gay stuff. It'd been the motivation for buying the dildo. The guys bottoming in the videos seemed to be enjoying pleasures his dick had never given him, and the idea of getting fucked intrigued him.

His dick was semi hard now, and he came back to the moment. He popped the cap off a bottle of lube he'd left in the shower, and stepped away from the water. He drizzled lube onto and along his middle finger, rotating it so the dripping lube covered all sides. Tentatively, he stretched his hand under his balls and placed his finger against his asshole. He circled and spread lube on it, enjoying the sensation. Pushing his finger deeper, he popped through the ring of muscle surrounding his hole, and he caught his breath. He pistoned his finger in and out a few times, spreading lube into his hole, then withdrew his finger and squirted more lube onto it.

This time, his finger glided in with almost no resistance, and he wiped the fingerful of lube around inside himself. He guessed that'd be enough, and took his finger out. He rinsed his finger off in the water and backed himself up against the dildo. The artificial cock tip bumped into his taint, sliding down towards his balls. He rocked forward and tried again, this time too high. He worried the lube on the dildo's tip would be wiped off, but he figured the lube in his ass would make up for it.

He reached around and held the dildo steady as he searched for it with his asshole. Bumping into it, he moved the dildo so it aimed right into his hole and pushed back. The replica cockhead burrowed into his asshole, trying to force it open. He remembered he needed to relax, and tried to untense his opening. The friction of silicone had felt nice at first, but now that his hole had actually started stretching it was hurting.

Jesse winced, and tried not to let the discomfort interrupt his relaxation. He pushed back harder while willing his hole open, and was rewarded with a sharp thrilling pain as his opening swallowed the dildo's head. He gasped and whimpered, holding still and trying to reconcile himself to the intruder in his ass. His dick had hardened when he was toying with his opening, but its desire to stiffen and strain felt at odds with his need to relax and accept. He started cautiously moving his ass in and out on the dildo, feeling the rubber shaft glide through his tender hole.

His hard dick bobbed and thumped his belly as he fucked himself. His ass felt nice, but still at risk of tensing up. He had to stand slightly on his tip toes to make the angle work, and it was hard to relax while straining his feet. The experience definitly didn't live up to what those porn submissives seemed to be feeling, getting fucked by real cocks. He braced his hands on the opposite wall, trying to focus on the pleasure and imagining himself getting plowed from behind.

The shower water ran over his shoulders and head, but some made its way down to his back. Water dripped over his ass, and he worried it'd wash away lube on the dildo. Surely he'd be getting somewhere soon; his ass was being fucked, but he didn't feel like he was building towards anything. Sometimes the dominant men in porn would jack off their sub while fucking them; maybe that would help.

He reached down and tried stroking his dick, but immediately knew it was a mistake. His ass closed and clenched around the dildo, and only by its absence did he realize there had been a growing excitement deep in his hole. He'd lost his craving for penetration, and the dildo just felt uncomfortable now. He pulled off of it, washed his ass clean from lube, and sighed in frustration. He turned the water off.

Stepping out into his bathroom, he looked down at his still hard dick. He could just jack off, but he knew he wouldn't actually feel satisfied. Resorting to his dick felt like giving up. His brow settled into a determined frown. He'd made an account on a hookup app recently, but hadn't actually used it or matched anyone. He hastily toweled off and grabbed his phone.

A few hours later, Jesse settled on Alice and Logan's profile. Jesse's ex girlfriend had introduced him to bondage, and it was one of the few things he missed from their relationship. Alice and Logan's bio said they were looking for a curious male sub for BDSM play, and he hoped if nothing else he'd enjoy wearing restraints again. Their bio linked to Alice's career and profile as a professional dominatrix, and Jesse browsed dungeon photos and customer ratings to satisfy him she was trustworthy. He fired off a message introducing himself, then got up to go grab dinner.

When he next checked his phone, he saw they'd already replied. His heart thumped as he opened it, seeing that they'd accepted him. They said he was exactly what they were looking for, and proposed he meet them Friday at 6:00PM. He sent back an affirmative, and fell into a nearby chair. Today was Wednesday night, and it felt suddenly real that in just two days he would apparently be having sex with absolute strangers.

His phone chimed, and he saw they'd sent instructions. He had to douche himself before coming, and his privates had to be hairless. He'd already gotten a douching kit when he'd gotten the dildo, and the fact they wanted him clean meant they were definitely going to fuck his ass. That was exciting, but shaving around his junk and anus was intimidating. Many of the submissives in porn he wanted to emulate were hairless, though, so he felt like this was a step in the right direction.

The next day at work, he was distracted the whole day thinking about the hookup. He read guides on hair removal and bottom prep during lunch break, and after work he swung by a store and got himself a combination male grooming trimmer set. At his house he spent a full hour that night angling a mirror up into his ass, trimming carefully till his pubes and balls and asshole were shaven smooth. He liked the way it looked and felt.

Friday dawned, and he could hardly think about anything besides Alice and Logan. He kept making mistakes in his work, and the last few hours of the workday dragged as he counted the minutes till he'd be off. He got home, showered, shaved his face, and cleaned himself out with the douching kit. He had an extra twenty minutes before he had to leave for the hookup, and he spent it restlessly second guessing what clothes to wear. At last, it was time to go, and Jesse navigated to the address they'd given him.

Jesse drove down a street in an upscale neighborhood, counting numbers on houses. Each house had a comfortably sized yard, and the cars in driveways looked nice. A few more driveways down and he found the address. A nice, black SUV sat in the driveway, and rose red curtains adorned the house's windows. Jesse parked on the curb acroos the street, and put his hands on the wheel.

His heart was thumping, and his hands were a little shaky. He felt excited, and very nervous. He'd never navigated any situation even remotely like this, and had no idea what he was walking into. He breathed in and out a few times, intentionally relaxed his hands, and stepped out of his car.

Jesse approached the house and rang the doorbell. The door was black with small gold filigree decorations around the edges. He could feel his heart beat louder, and he uncertainly moved his hands around, trying different positions. Should he already be trying present himself as a sub? Footsteps approached behind the door.

The door swung, revealing Alice. She wore a robe made of thick black material, and inside it he glimpsed a corset. He noticed a burnished red ring on her left hand holding the door, then stepped inside as she waved him in. Beyond the door, Logan leaned against the wall, wearing jeans and a relaxed-cut collared shirt. He was heavyset and clearly strong, and a bit taller then Jesse.

"Hi, welcome to our house, " Alice said by his side.

Jesse gulped and turned to her. "-thanks! I, uh-"

"First Rule," Logan said, stepping away from the wall, "You will not speak unless asked a question. You will always address us as Sir and Madame."

Jesse nodded, goggling at him.

Sir held up his left hand, and Jesse saw a red metal ring on his ring finger, matching Madame. Above the ring was a wider black silicone band. Sir took it off, and gestured for Jesse to hold out his hand.

"Second, " he said, slipping it onto Jesse's middle finger, "this: is your safeword. Try giving the ring a hard quick press with your thumb."

Jesse looked at the band, a little embarrased that only his middle finger was big enough. He pushed his thumb into the center of the band, and a loud clear ringtone sang out from Sir's pocket. Sir took his phone out, and the screen was glowing bright red.

"That means stop. You can always halt the scene at any time, for any reason. Please don't hesitate or worry we'll be disappointed, we want you to have a good experience. Now, try giving it a long press."

Jesse did, and after half a second Sir's phone's screen lit up yellow. A softer chime ringtone played.

"If you need us to go easier but you feel comfortable continuing the scene, give a yellow signal. Do you understand?"

Jesse nodded.

"Good," Madame said. Sir slipped the phone back into his pocket. "Third rule," she continued, "You will always wear this while in our house."

She pulled out a thick black strap from underneath her robe, with a D ring and a buckle on it. She stepped forward and curved it towards his neck, and Jesse recognized it as a leather bondage collar. She buckled it snug around his neck, and gave it an appraising tug. She stepped back.

"Now; take off your clothes."

Jesse glanced at both their faces, and they simply stared expectantly at him. His continued nervousness was balanced by relief that they'd given him a clear role to fall into. He hesitantly tugged off his shirt and kicked off his shoes. They didn't move or give any signal, they just continued waiting.

He undid his jeans, and got his foot caught as he pulled the first leg off. He hopped on one leg once or twice, struggling with it. When he straightened and stepped out of the other leg, he was blushing a little. It was embarrassing to hop and prance for two strangers, while they watched him undress. He felt his shame was keenly observed. They seemed very interested in his reaction to all this.

Looking down to pull down his underwear, he realized his dick was rising a little, tenting out the front of his boxers. He blushed for real now, feeling pinned down by their gaze. The humiliation seemed to be what his dick wanted, because it hardened even more, pushing stiffly into the fabric.

He instinctively wanted to turn away, to hid his dick, but he knew doing so would just be more embarrasing. He bent, pulled the elastic band of his boxers over his dick, and let them drop. He stole a glance at their reaction to him, and saw they looked amused and pleased. He stooped and pulled off his socks, feeling every bounce and flop of his dick. When he straightened, nude, his face was dark with shame.

"Follow me," Madame said, turning and walking down the entry hall. Jesse trotted after her, feeling Sir's gaze on his ass as Jesse walked away. She walked ahead of him down a hall, then into a bedroom. It was tastefully decorated, and the bed's blankets were deep blue. Nearby, on a bedside table, sat a black silicone butt plug and a small lube bottle. Madame pointed at the plug.

"Put that in and wait for me." She turned and left him, closing the door behind her.

Jesse walked over and looked at the plug. It's neck looked nearly as thick as his dildo, and he knew he'd have to work up to it. He grabbed the bottle of lube, and dispensed some onto his fingers. He lay back on the bed, legs drawn up, and started gently nudging his hole.

Laying down, with his naked back rolling into rich blankets, he had a much easier time relaxing. His hole welcomed his middle finger, and after gently fucking himself for a moment Jesse added a second finger. He could feel his sphincter slipping and winking and pulsing against his insistent fingers, and he closed his eyes. It was obvious his hole would have to endure a lot tonight, but he felt ready for it.

He pushed in a third finger and writhed it alongside the first two, but really he wanted the plug. He wanted something foreign inside him, that would push and compel in ways his fingers couldn't. He pulled his hand away from his ass and slathered lube from his fingers onto the plug, careful to coat the lower flared neck where it would rest against his opening. He drizzled more from the bottle onto the tip of the plug, watching the lube slowly wash down the sides. He didn't want to get any lube on the blanket, so he stood up from the bed to put the plug in.

He tried planting one foot on the floor and one on the bed, stretching his ass cheeks apart and hopefully giving good access to his hole. When he actually tried putting the plug in, however, he quickly knew he wouldn't be able to relax enough while standing like this. He clambered back on the bed, putting his face and chest down into the blankets while planting his knees and sticking his ass up into the air.

This felt like a position that he could get fucked in, and his dick which had started to subside hardened again. He breathed in and out, in and out, and imagined a cock pushing down against his hole. He pushed the plug into himself, gradually increasing the pressure while focusing on the imaginary dick and pretending it was the plug. He flinched and squirmed, but kept pressing the plug harder.

His stretching sphincter finally overcame the widest part of the plug and sucked it in down to its neck, and Jesse cried out into the blankets. The pressure of his hole trying to close on the neck kept the plug pressed into him, and Jesse felt incredibly full. He awkwardly rolled over onto the edge of the bed, and tried standing up, getting used to the plug inside him. His dick throbbed.

Madame had said to wait for her, and he wondered how he should present himself. For a few minutes he knelt on the floor facing the door, but although it was a comfortable angle for the plug his knees grew sore and he gave up on that position. He pushed himself back on the bed, and lay down. His dick had stayed excited all while he waited in a submissive posture, but it started to grow soft now. He settled into the blankets and waited.

Jesse didn't hear her approach, but the door suddenly opened. Madame stood in the doorway, now without her robe. She had knee length heeled boots and a black leather leash hanging across one shoulder.

She strode into the room, tossing a black bag onto the bed.

"Did you put it in?"

Jesse nodded. Even when asked a question he instinctively didn't speak.

"Show me, " she said, making a twirling around motion with her finger.

Jesse clambered off the bed and turned around, so she could see the plugs base between his ass cheeks. His humiliation and erection both returned, and he suspected that was the sole purpose of making him display himself.

She stepped closer behind him, and he was going to turn when she grabbed both his wrists hanging by his sides. She positioned his arms behind his back so that each of his hands grabbed his other forearm, then reached into the bag on the bed and pulled out leather cuffs. She cuffed him so that his arms stayed pinned, then spun him back facing her.

She leaned in and kissed him, then her eyes fell down to his stiff dick poking upright. He was glad he wasn't supposed to speak, the conflicting emotions washing over him left him feeling very muddled.

Turning to the bag again she pulled out a bottle of lube, and a small white cloth enclosed sack. She left the sack on the bed and popped the bottle's cap, squeezing a few drops onto her fingers.

Without warning she reached out and grabbed his junk, massaging the lube evenly over his dick then his balls. It wasn't a handjob, her only motions were to spread the lube, but it felt good. She squeezed another drop of lube onto her thumb, and pushed it in a circle around the base of his balls. She had a slight knowing smile, like she could read his wondering mind. He let himself stop guessing where this was going and just enjoyed the sensation.

Leaving one hand on his balls, Madame replaced the lube into her bag and picked up the white sack. She applied it to his junk, and Jesse gasped. He would have yanked back involuntarily if she hadn't still been gripping his balls. It turned out to be some sort of freezerpack, and it was icy cold.

She held it on firmly until his erection died down, which didn't take long. Dropping the sack she reached into her bag again and pulled out something shiny and metallic. Jesse glimpsed a cock ring with a small cylinder piece before she put it over his cock. Even with Jesse soft, the ring was tight, and she had to pull his testes through one at a time to get it onto the base of his junk. It felt cold, but snug, and he found he kind of liked it.

She pulled a second metallic object from her bag, and with another start he recognized it as a chastity cage. He could see the cylinder hole piece where it locked into place with the cock ring. She slid it pretty easily onto his soft dick, but raised an appraising eyebrow. "You shrink nicely, " she said, smiling, and took another cage from her bag. She pulled the first one off and once they were side by side Jesse saw the new cage was smaller. She had to squeeze and handle his soft dick to get it into the cage, but once it locked into place it felt snug but not tight.

Jesse hadn't imagined this at all, but she didn't honor his surprised face with any reaction. At last she took the leash off her shoulder, and grabbed the metal clip end. Jesse raised his neck to give her access to the metal ring on his collar, and she stroked the underside of his chin while holding his leash.

He didn't feel her actually clip it onto his neck, though, instead he felt the metal clip graze down his chest then his stomach. He looked down just in time to see Madame clip the leash onto the front of his cock cage. Jesse glanced up in surprise but she'd already turned and started towards the door, tugging him forward.

He stumbled a little without his arms to balance him, but he caught his footing. The cage weighed on his balls, and the plug pushed and moved inside him as he walked. Madame didn't look back as she led him around a corner and through a doorway down a staircase.

The lower level was an expansive room with a large matte black pad in the center of the floor. Blinds covered the windows, but they let in diffused ambient light from the backyard. Sir was crouched on one knee on the black pad, one hand holding a spray bottle and the other wiping long strokes with a cleaning cloth. He turned and stood when he heard them approach.

Sir was naked, and his cock was partially erect. Jesse noticed he wore a burnished red cock ring matching his wedding ring, and that he was circumcised. He was hairy, and powerfully built.

Near him, a low chair was pulled up facing the pad. On an adjacent end table Jesse saw a butt plug and a strapon among other bondage implements. They looked large. Madame had moved behind him while he stared at Sir, and she now slipped a blindfold over his head. She left it a little high, so he could glimpse his feet and the tip of his cock cage if he looked straight down. Madame walked ahead of him again, pulling him towards the pad.