Online Chastity Ch. 07

Alex Couldn't believe what he was about to do. Sitting in his empty apartment he re-read his resignation letter for the twentieth time. How had it come to this? Over the past four weeks he had given up everything he had built his life towards. His career, his apartment, all his belongings. Everything that had previously defined him was gone. He had told his family that he was going to travel for a year. That he was going to "find himself." He had even found a few retreats in various parts of the world that offered technology free experiences to justify being unreachable.

Sam was waiting in the car downstairs. She had told him that they were going to her property out in the country. Alex was excited. He was scared. He was constantly feeling new things every moment he was with her. Sam satisfied every fantasy he had ever had... and so much more. She had also used his fantasies to take complete control of every aspect of his life. Part of him loved it. The other part was screaming in the back of his mind that things had gone too far... but it didn't really matter. At this point, he couldn't escape Sam's control, even if he wanted to.

Looking back, Alex realized that from the moment he had chosen to re-lock his chastity in Sam's apartment, he had given up this life. That was his last truly free decision.

Alex hit send and his resignation was submitted.

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FOUR WEEKS EARLIER

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The day had been overwhelming, to say the least. Sam had done her "interrogation," discovering everything that turned Alex on... including some things that he hadn't even realized himself. She then humiliated him in front of Tam, which as it turns out turned him on even more. After he had put on a show for them, Sam had re-locked his chastity device while Tam watched through the mirror. Only then did she remove the arm binder and gag. Sam then unhooked his leash from the ceiling.

Tugging on the leash, Sam led Alex out of the room and into her bedroom. Alex nearly rolled his ankle a few times as he continued his crash course on walking in heels. The padlock that held the eyelets in the shoes together clacked each step, reminding him that the heels were not going anywhere. As Sam started tugging the leash towards the living room, he stopped, and the leash went taut. Alex couldn't face Tam.

"I promise you that what you just did was far more humiliating than sitting with us. Tam has some questions for you. I have told her a few things, but this is all very new to her. You are going to answer her questions and then she is going to go." Sam said, matter-of-factly.

Alex, having just cum multiple times, wasn't really in the right head space to enjoy the humiliation. What good would refusing do, though? She would shock his collar... or leave him locked up in chastity... He couldn't even leave; his clothes were still out of reach in the duffle bag hanging from the ceiling.

Seeing the look in Alex's eyes soften, Sam tugged on the leash again and Alex followed. Sam sat on the couch, opposite the chair that Tam was in, and had Alex kneel at her feet. Tam was grinning from ear to ear. She asked how Alex wound up in this position and Alex was unable to answer. His cheeks were red, and he was covering his chastity with his hands.

Sam gave his collar a little shock. "From this point forward, you will answer every question with complete honesty. You will not talk back. You will continue to end every sentence spoken to me with 'Miss,' and when Tam asks you a question, you will end with "Ma'am. Do you understand?"

Alex was speechless once again. Was this really happening?

Sam shocked him again.

"Yes, Miss!"

"Good boy."

Tam was thoroughly enjoying the look on Alex's face as Sam explained Alex's predicament to him. She could tell he was getting turned on again too. Even after cumming multiple times, being put in his place like this was making his chastity device move.

"Are you turned on?" Tam asked.

"Yes, ma'am."

"Put your hands behind your back, pet. Tam has never seen a chastity device before." Sam ordered.

Alex did as he was told.

The next hour was very strange. Sam and Tam had drinks. Tam asked questions of Alex and he answered. Tam asked questions of Sam, and she answered. It was like three friends hanging out... except Alex was naked, locked in chastity, high heels, a collar, and would be shocked if he didn't tell the truth. The questions were ones that he had never answered aloud before. Some of them were questions that he may have even answered differently before Sam's interrogation. He learned a lot about himself in that process as well. It was utterly humiliating... and as it turns out, humiliation really turns Alex on.

Tam didn't know all that much about Sam's history... She had only started working at the coffee shop a few months ago and they were always friendly, but until yesterday, all she really knew about Sam was that she was the tenant upstairs who her manager insisted got free coffee any time. Sam had let Tam in on Alex's little secret to enhance Alex's experience in that first meeting. She also didn't want to have to explain why she was wearing a latex catsuit in the middle of the coffee shop... so Sam opened up a little to her favourite barista. She told Tam that she liked to be in control and that someone was coming to meet her locked in chastity and she was planning to tease him thoroughly. To Sam's surprise, Tam really enjoyed the idea. She wanted to know more. Sam told her that if things went according to plan, she would show Tam what a submissive man could be.

Tam was enthralled. She was asking non-stop questions. It was like a toddler discovering that art meant more than drawing with crayons. She needed to know everything. How long had he wanted to be locked in chastity? Why did he like it? Is he happy now that Sam controls him? How does he feel about Tam having a video of him cumming the way he had? Does he like wearing the high heels? Is this turning him on? What does he want to do to Sam right now? What does he want to do to Tam right now? What does being locked in chastity do for him sexually? Has he ever wanted to be in control, or is this his ultimate fantasy? Does he want to get fucked in the ass? If Sam had a strap on right now, would he suck it? Does that turn him on? How often did he jerk off before he was locked in chastity? When was the last time he got laid properly?

The questions went on and on. Alex, fearing the shock to his collar, answered as instructed. He told the truth, always ending with Miss or Ma'am, depending on who he was talking to. It was turning him on again and when Tam asked about that, he had to admit it.

"Can you get a pet for me?" Tam asked Sam with a grin.

"Do you want to feel like you are in control?" Sam asked, grinning back.

"Uh, yeah!"

With that Sam gave Tam a small remote control. "I can control everything from my phone, but this is the remote that came with collar. I want to see what you would make him do."

"Really?" Tam's eyes went wide with excitement.

"Really. Do not shock him unless he disobeys you, though. And if you ask anything that I don't want, I'll intervene."

The two looked at Alex who was suddenly very nervous.

"Get on all fours." Tam ordered.

Alex looked at Sam. She nodded, as if her permission was what he was looking for. Truthfully, he just couldn't really comprehend what was happening anymore. He had fallen into the submissive rabbit hole and there was no way back out. He got on all fours.

"Slap your own ass." Tam instructed.

Alex did.

"Harder."

Alex did.

"Stand up."

Alex did.

"Come over here. I want to see your chastity device."

Alex walked over to Tam and stood in front of her. Tam looked to Sam. "Do you mind if I touch it?"

"Be my guest." Sam responded with a grin.

Tam took the chastity in her hand and lifted it up to see how it was locked on. She tugged on it a little. "So, you really can't take this off?"

"No, Ma'am."

"Isn't sex part of the fun with having a sex slave?" Tam looked to Sam.

"I could have sex with him if I wanted. I could make him have sex with you if I wanted. Some people use chastity as a way to prevent pleasure, but for me it is purely to control it. He will only have pleasure when I allow it. He will only cum when I allow it. If I didn't let him cum at all, he could leave, and his situation would not change. It's his need to cum that will keep him coming back. The fact that being locked in chastity turns him on, only helps to build his desperation more quickly."

It was humiliating to hear Sam talking about him as if he wasn't in the room. Explaining how owning his orgasms is what gave her control. Knowing that's what turned him on. She was right though. And there was nothing he could do about it.

"How is he with his tongue?" Tam asked.

"I don't know yet." Sam replied. "Doesn't really matter where he's starting from though, he'll learn."

"Can I find out?"

"No." Sam said. "I need to break him in properly first."

Tam was disappointed. She tapped the button on the collar and it shocked Alex. His hands shot to his neck. "Just wanted you to know I could." Tam said.

"Give it to me." Sam looked very serious.

"I was just messing around." Tam was surprised by Sam's tone.

"That's not how I do things. If you want to be involved in this world with me, you need to learn the rules first. Control is trust. Trust that if you do what you are told, you won't be punished."

Tam gave the remote back to Sam. "Okay, sorry. Can't you just... do what you want, though?"

"To a degree, but control is based on trust. If I say I'm going to do something, I do it. If I am using a shock collar to punish bad behaviour, what good does it do if my pet thinks it might get shocked at any time?"

Tam didn't look entirely convinced. "Right. Of course."

"If you really want to learn, I'll help you. For tonight, I need some time alone with my new pet."

"Well, thank you for showing me... everything." Tam turned to Alex. "Good luck."

Sam saw her out, locked the door, and turned back to Alex. "I'm sorry about that."

"It's okay, Miss."

"It's not. I shouldn't have given her the remote. She wasn't ready. I want you to know that I will only shock you when you deserve it, and our goal is for you to avoid getting shocked. Wouldn't you agree?"

"Yes, Miss."

"Good. Are you enjoying yourself, pet?"

"Yes, Miss."

"Good. Do you need to be home for anything tonight?"

"Just work tomorrow, Miss."

"That's disappointing but I understand. I want to watch some TV before you leave. Kneel in front of the couch."

Alex did as he was instructed. Sam was wearing a skirt that she hiked up before sitting on the couch, her legs on either side of Alex. "When Tam wanted you to lick her pussy, did you want to?"

Alex didn't know how to respond.

"It's okay, pet. I can tell you are attracted to her as well."

"Yes, Miss."

"Do you want to taste me, pet?"

"Desperately, Miss."

Sam lifted her legs into the air and shimmied her panties off. She held them out in front of Alex. "Put these in your mouth, pet."

Alex did. Sam's panties were already very wet, and she tasted incredible.

Sam rested a foot on both of his shoulders. "Put your hands behind your back." Sam ordered. "When I tell you to get in position, this is your place. On your knees in front of a chair, ready to please me with your tongue. Do you understand?"

Alex nodded as he clasped his hands behind his back.

"Good boy. Give me my panties back."

Alex opened his mouth and Sam pulled her panties out as she slid her feet past Alex's head. Bending her knees, her legs forced him closer to her pussy. "You don't lick until I tell you to."

Alex was staring at her pussy. He'd never wanted to please a woman so badly. His cock was straining in its cage.

Sam opened her phone and tapped a button. The TV behind Alex turned on. "Now... what do I want to watch?

Alex moaned with anticipation, moving closer to Sam's pussy.

"Not yet." Sam put a finger on his forehead.

Scrolling through her streaming services, Sam landed on Severance.

"Do you like sci-fi, pet?"

"Yes, Miss."

"Me too." Sam hit play and pulled Alex towards her pussy. "Now make me cum."

As Alex's lips touched Sam's pussy, he looked up at her. Eyes like a puppy dog.

"This is where you belong now, pet. You cum when I allow it. You make me cum whenever I ask. I really don't like shocking you. I would much rather control you with your sexual desperation. Do you understand that?"

Alex nodded as best he could while being held against Sam's pussy.

"Good. Let's see how you do."

With that Sam turned her gaze to the TV. Alex had pleasured a few girlfriends with his mouth in the past. He had never had any complaints.

Alex started slow. He kissed Sam's pussy gently and looked up to see a smirk on her face. She didn't look down from the show, however, so Alex continued. He slid his tongue inside her and realized just how wet she was. Her juices covered his lips and dripped down his chin. Sam's pussy was incredible. She was hairless and tight. She tasted sweet and womanly. She had clearly been turned on for a while and the taste of her desire was driving Alex wild. He desperately wished he could slide inside of her.

Trying to ignore how tight his cage was getting, Alex licked Sam slowly from bottom to top and rested his tongue on her clit. Sam inhaled sharply, giving Alex a little bit of confidence that he was, in fact, pleasing her. She was really enjoying it and he was determined to make her cum just as hard as he had cum earlier. He would prove himself to her right now.

As soon as he started to swirl his tongue in circles around her clit, Sam grabbed the back of his head and spread her legs a little more.

Alex continued, dipping his tongue inside of her, pulling her juices up to her clit and then swirling his tongue around it over and over again. Sam came faster than Alex expected. She held his head firm and pushed his mouth into her as every muscle in her body tightened up.

She didn't squirt exactly, but she was so wet as she came that holding Alex's face in her pussy, covered him in her juices.

Alex was all smiles. He had clearly done a good job. He was proud of himself. He wanted to please Sam and he had.

As Sam's body relaxed, Alex started to pull away.

"Where are you going, pet?"

"You just came, didn't you, Miss?"

Sam laughed, grabbed her phone, and paused the show. "Is that a question? Do you have any doubt that I just came?"

"No, Miss."

Sam put a hand on Alex's cheek. "You will never have to guess if I've had an orgasm. I was trained for that."

"What do you mean, Miss?"

"I mean that when I was in your position, I was trained to cum exactly how Terry wanted me to cum." Sam took a breath and thought back to her times as a sub. "He trained me to be constantly horny. He trained me to cum almost immediately when stimulated. By the end, he kept me so turned on all the time that he could make me cum on command. Just knowing that's what he wanted, my body would oblige."

"Wow."

Sam tapped a button. Alex's collar gave him a shock.

"You end every sentence with 'Miss.' Understand?"

"Yes, Miss." Alex reflexively reached for his collar.

Sam got up and walked away, leaving Alex wondering what was happening. Kneeling in front of the couch, he shifted back and forth a little from knee to knee looking for a little relief. He tugged on his collar. It wasn't going anywhere.

Sam returned with a pair of hand cuffs. "When you are in position, you don't get out of position unless I instruct it. That includes keeping your hands behind your back. If you can't do it on your own, you will be cuffed.

"Yes, Miss." Alex obediently put his hands behind his back again.

Sam cuffed Alex's hands and sat back down, putting her feet back on Alex's shoulders. "There were two outcomes from my training with Terry. Firstly... I eventually realized that my place is not as a submissive. I was meant to rule. Wouldn't you agree?"

"Yes, Miss."

Sam smiled. "That took a little bit of time to figure out, but eventually, I found my place. The second result of his training, and something I realized far too late, is that what he did to me can't be undone. I cum hard, I cum fast, I cum repeatedly... and I crave it all the time."

Alex sat on the floor between Sam's legs, obediently listening.

"When I cum I am satisfied for about ten seconds... and then I want more. I need more. You can't undo years of sexual training, pet. Even if your mind changes, your body will crave the things it is made to crave. Kind of makes you wonder what I'm going to do to you, doesn't it?

"Yes, Miss." Alex looked nervous.

Sam grinned. "I am going to call on you to pleasure me often. More than you will want. More than your mouth will be able to handle at first. But this is your place now. This is where you belong. You are my plaything, and your soul purpose is to pleasure me. Isn't that what you've always wanted?"

"Yes, Miss."

"Good. Now get back to work." Sam un-paused the show and pulled Alex into her pussy again with her feet.

Alex did as he was instructed. By the end of the episode, Sam came fifteen times. Alex's jaw was aching and his tongue was soar... He didn't know tongues could get soar.

Sam turned off the TV. "You did good today, pet. Are you happy that I own you now?"

"Yes, Miss."

"Good. Not that you really have a choice anymore." Sam grinned. "You're going to go home now. You're going to look around at your things, at your previous life, at everything you were before this moment, and you're going to realize that where you belong is between my legs. Pleasuring me on command. You're going to realize that you made the right choice today. That there is no turning back. You are going to think about everything that's happened to you and realize that it is turning you on more than every fantasy you've ever had, and you're going to wish you could jerk yourself off... but you can't. Your cock is mine. Your orgasms are mine. You will only have access to your cock when I allow it from this point forward. That's how you want it to be, isn't it?"

Alex's cock hadn't ever become fully soft since going back into its cage, but this was different. He was fully straining inside his chastity now. Feeling just how tight it could be. This speech felt very... final. Like his decisions today couldn't be undone. It scared him. It also turned him on.

"Say it, Pet." Sam stared into his eyes.

"Yes, Miss."

"Your chastity and collar will remain locked on. Your clothes will stay with me." Sam walked away once again, leaving Alex stunned. When Sam came back, she held a few articles of clothing and a small steel box with a blinking red light on it. "Stand up." Alex did and Sam unlocked his cuffs. "You can wear these to get home."

Sam handed Alex the clothes. It was a skirt and a tight leopard print top.

"Please don't make me go out like this, Miss."

"Pet, I know for a fact that you want me to force you to wear women's clothing. I know the humiliation of it turns you on. I can see your cock straining its cage at the thought, so don't pretend like I don't know what's best for you. Put them on."

Alex did as he was instructed.

"This contains the keys to unlock your high heels." Sam handed Alex the steel box.

Alex, looking down at himself, saw the heels Sam had locked on him earlier in the day below his new skirt. So much had changed.

"The box will only unlock when I send it the signal." Sam held up her phone. "And I will only do that once you get home and send me a photo of you in position on your kitchen floor. When you get in your car, I would suggest you do a couple laps around the parking lot to get used to driving in heels before you hit the main roads."