Online Chastity Ch. 01-06

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When Alex heard the door open, his cock sprang to attention. Sam was back. Moments later, he heard her walk into the room and step up in front of him. He moaned into the inflatable gag.

"Hi pet." Sam whispered into his ear. Alex could hear the smile in her voice. "Did you miss me?"

Alex nodded and moaned "yes" as best he could.

Cupping Alex's balls with her hand, Sam asked: "Have you been hard all this time for me?"

Alex shook his head and continued to moan as Sam fondled his aching balls.

"Well, I'm glad that my presence alone is enough to make you hard. I bought some things for you, pet. Would you like to try them on?" Sam let go of Alex's balls and stepped away as he moaned, clearly nervous.

"Are you scared, pet?" Alex Nodded, despite his cock getting harder. The fact that Sam had started calling him pet was not lost on him. The interrogation had revealed a few desires that even Alex wasn't aware he had, and Sam was clearly leaning into them.

"I'll tell you what. I'm going to put a few things on you, and if you behave, I will give you the opportunity to cum. Are you going to behave?"

Alex nodded furiously.

"Good. Lift your left foot." Sam instructed as she unclipped his ankle cuff from the wall.

Alex did and quickly realized she was putting a shoe on him. When Sam made him put weight on it so he could lift his right foot, he realized it was a high heel. He moaned again and took a second to find his balance. When both shoes were on, he heard two clicks.

"Don't you look cute, pet." Sam whispered in his ear as she locked a collar around his neck.

Alex moaned into the gag as he heard another click.

"Don't pretend you don't like this." Sam put a finger on the tip of Alex's cock and pushed it down a little. It was rock hard and sprung back as soon as she let it go. "I'm going to unlock your hands now so that I can put them in a single sleeve arm binder behind your back. I know you want to wear it for me... but I'm concerned that in your desperation, you might reach for your cock. Are you going to behave?

Alex nodded.

"Are you sure? We could wait until you get soft and lock your chastity on again just to be certain."

Alex shook his head side to side vigorously.

"Alright. If you touch your cock, you will be punished. Do you understand?"

Alex nodded.

With that, the hook released from the wall and Alex was able to pull the chain between his wrist cuffs off it. His arms had gone numb from being over his head for so long and he shook them out in front of him. Sam released the cuffs and rubbed his wrists. "Poor thing. Let's get these locked away again, shall we?" Sam took a step back to get the arm binder.

Alex hadn't intended to lie to Sam. He actually thought he would be able to behave in the moment... but the chance to cum, and his desperation to clear his foggy mind left him feeling that any punishment would be worth just one orgasm. His hand moved to his cock, and he started to stroke it. He just needed to get off once so he could think straight again... ZZZZZTTTT

Alex's hands immediately shot up to his neck, but the collar that had just shocked him wouldn't budge. He found the padlock keeping it secured and pulled off his blindfold, looking at Sam desperately as his eyes adjusted to the light.

"I had a feeling that might happen. Don't worry, you'll learn to behave. Hands behind your back." Sam motioned, holding the single sleeve in one hand and her phone in the other.

Alex moaned into the gag, a whole new level of desperation sinking in. He looked down at his cock and saw his feet for the first time. They were in black lace up heels that curved perfectly around his ankles. The heel must have been 5 inches and if he had seen these on Sam, he would have thought there were incredibly hot. The laces were tied in a nice bow on the second to top eyelets. The top eyelets had a small padlock through them, securely locking his feet in the shoes. He pulled on the gag, but it was locked on as well. His hands went back to the collar. As he looked back up at Sam. She was smiling.

"You've gotten yourself into quit the predicament here, pet."

Alex's eyes were pleading as his hand instinctually dropped back to his cock.

Sam tapped her phone and his collar shocked him again. Alex's hand shot back up to the collar. "That was twenty five percent of what this collar is capable of. Would you like to try fifty? Or do you want to put your hands behind your back and turn around?"

Alex did as he was told and before he could think twice, Sam was sliding the single sleeve over his arms and securing it around his shoulders. His hands were, once again, completely useless, this time trapped behind him.

"Isn't that better, pet?" Sam said as she stroked his cock once, looking him in the eye and then letting go.

Alex thrust against the air, almost losing his balance in the heels.

Sam pulled a leash out of a shopping bag and clipped it to a d-ring on his collar. With a little tug, she led him towards the door leading to the room behind the mirror. Alex had no choice but follow. Thankfully Sam took it slow as he learned to walk in high heels for the first time, nearly rolling his ankles with every step.

Through the door, Sam guided Alex towards a platform. It was dark in the room, aside from the light coming through the one-way mirror. Looking into the living room, Alex's stomach turned inside out, and his heart began to race. Tam, the barista from the coffee shop, was sitting on the overstuffed couch opposite the chair Sam had been sitting in previously. Alex looked at Sam and pleaded with his eyed, shaking his head, but all Sam had to do was gently tug on his leash and Alex was made to follow.

The platform wasn't the same as Alex had imagined it from Sam's story, though. She had prepared it for him. There was no steel cock on a pole, in its place was a silicone cylinder that looked very much like a pussy.

Sam looped Alex's leash onto a hook in the ceiling that placed him right in front of it, making it impossible for him leave the platform/view from the living room should the lights be turned on.

"As you know, while the lights are off, no one can see into this room. When the lights are on, however, the living room mirror becomes a window."

Alex started to back away.

"Be careful pet. The hook that I have attached your leash to is attached to the switch that turns on the light. If you tug on it, the light goes on. If you let the leash go slack again, the light will go off.

Alex moaned behind his gag again, looking between Tam and Sam. There was not a lot of slack in the leash as it was... he was stuck here in the middle of the room. Front and centre.

Sam lowered the silicone pussy just enough so that Alex would have to bend his knees awkwardly to get his cock into it. It was also just low enough that it would cause him to tug on the leash and turn the lights on. "I told you I would give you the opportunity to cum. It's up to you now." Sam grinned as she poured some lube over his cock, stroked it a few times, and then walked away.

Alex watched Sam walk out into the living room to greet Tam. They had coffee cups on the table and the two of them got comfortable, sipping their coffee, and talking like old friends. Sam made sure to sit so that she was facing the mirror.

Alex was desperate. He needed to cum. Sam had already seen him naked and humiliated... maybe he could just get off really quick and Tam wouldn't see?

Alex shifted his footing slightly, heels clicking as he spread his legs a little. His mind continued to race with question of how and why he had gotten himself into this situation. Locked in heels, arms restrained, shocking collar locked around his neck, gagged, and a leash positioning him for unavoidable humiliation if he wanted to get off. Desperation took over and he realized that as humiliating as this was... he couldn't deny how much it was turning him on. Was that just his need to cum talking, or did he like being in this position?

Alex bent his legs, separating his knees wide enough to keep his balance in the heels. As soon as the leash became taught, the light turned. He immediately stood back up, and it turned off. Sam had been watching and was grinning from ear to ear. Tam looked over her shoulder to follow Sam's gaze but all she could see was the mirror. When Tam turned back, Sam giggled and the two started talking and drinking coffee again.

Alex bent his knees just enough so the leash wouldn't pull... but he couldn't quite get low enough to slide his lubed-up cock into the silicone pussy. He took a deep breath around the gag and sunk lower. The lights flicked on. He had to pull on the leash with his weight a little to get low enough that his cock could find the opening of the silicone. Collar pulling on his neck, he managed to get it in and started fucking it as fast as he could. Sam grinned again and Tam turned around, her eyes going wide at the sight. Alex pulled his cock out and stood up as fast as he could, almost tripping. He managed to find his footing and thankfully let the leash go slack, plunging him into darkness again. He was so close already. He just needed a few more seconds and he could have gotten off... but now Tam had seen him... How could he possibly show himself here or in the coffee shop ever again?

Sam and Tam stood up, pulled two chairs in front of the mirror, and sat back down looking right into it. Tam's expression was one of delight.

Alex moaned into his gag.

Sam knew from the interrogation of his cock that the idea of being humiliated in front of women turned him on. She knew that the idea of being forced to wear high heels turned him on. She knew that being treated as her pet would turn him on.... And she knew that being forced with inescapable bondage and true physical control over his cock was the thing that turned him on the most. He would have never admitted to any of those things out loud, but she had captured him, put him in this position, turned him into her pet, and it was clearly everything had ever wanted... even if he hadn't realized it himself yet.

The situation pushed Alex's desperation to the breaking point. He looked at Sam and Tam, then down at his cock and the silicone pussy just below it, his only means of getting the release he needed.

Sam and Tam sat in front of the mirror for a few minutes. Alex watched as Tam asked all sorts of questions he couldn't hear. Sam answered them all, casually sipping her coffee and smiling as she looked into the mirror, seemingly straight into his eyes.

Alex couldn't think straight. It wasn't that he was considering whether or not to get himself off in front of them, it was going to happen. He was just desperately trying to hold out for as long as he could, willpower crumbling with every second as his need to cum consumed him.

Alex bent his legs until the leash pulled taut and the light flicked on. Sam and Tam both looked up, watching as he slid his cock in the silicone pussy. Alex wasn't sure how much Sam had told Tam, but she seemed to enjoy what she was seeing. So much so that she pulled out her phone and started recording. Alex wanted to pull his cock out and stop... He desperately wanted to make the room go dark so she couldn't record him... but it was too late for that now. He had reached the point where there was no turning back. His cock needed to cum more than his mind could convince him it was a bad idea.

Alex fucked the silicone pussy for 4 seconds. His legs bent, heels clicking as he kept his balance, arms pulled back and locked behind him, collar pulling just enough to make him feel the strain around his neck, and with two women watching him, utterly humiliated, he came harder than he had ever cum before. He pushed his cock in as hard and deep as he could and in that moment realized that there was no back to the silicone pussy. He shot his load all over the back of the mirror.

Sam and Tam thoroughly enjoyed the show.

Alex was breathing heavily around the gag as his head finally started to clear. Reality crashing down around him. It's amazing how much you can justify when you're horny enough... He looked at the two women, moaned into his gag, pulled his cock out of the silicone pussy, and stood up, sending the room into darkness once again.

Sam and Tam were laughing and talking as Sam pulled out her phone and tapped a button. It opened an intercom to the room.

"Pet, Tam thinks you came too fast. She would like you to try again."

Alex's cock hadn't even had a chance to get soft yet, but his inescapable, humiliating situation, followed by this simple message from Sam letting him know just how in control she was, had left him feeling like he might be permanently erect. He was living through a fantasy that he didn't even know he had and even immediately after he found the release he so desperately needed, the need to cum was already building inside him again.

"Pet, stick your cock back in and cum again for us."

Alex moaned into his gag as he contemplated why this was turning him on so much. He thought about his options for a little too long, and the shock to his neck snapped him out of any thinking he was attempting to do. Alex instinctually bent his knees, the lights turned on, and he slid his cock back in, following orders and preventing another shock.

"Remember, pet, I don't like asking twice. Now cum again for us."

Alex started fucking the silicone pussy again. Utterly humiliated... and more turned on than he had ever thought possible...