To Catch a Sub - 009

Newandwilling -- Yes Sir.

Tony watched as Sasha sat for a few more seconds and then began to work herself up and down on the huge black dildo. The first few times she was tentative. Taking her time to withdraw it and then easing back down on it slowly. After the third stroke, Tony saw her eyes change and she began to work herself up and down vigorously. By the tenth stroke, she was panting heavily. Her tits were bouncing up and down with the rapidity of her movements. She was pulling the dildo out almost to its full length and then almost falling back onto its length. The coffee table shook and shuddered each time she rammed herself back down onto the table. He was afraid she would break the table before she managed an orgasm.

Sasha was lost in the sensations. It was the most incredible feeling she had experienced so far. She was actually getting fucked instead of just feeling the pain. Still, without using her hands on her clit of pussy, she was having a hard time getting herself to the edge. She concentrated more and her memory recalled one of the videos she had watched recently. She let the video play out in her mind and it wasn't very long until she slammed down on the dildo and screamed in ecstasy as she vibrated and twisted on the dildo with a shattering orgasm.

Tony watched in fascination. He let her sit there for a few minutes. He typed a message for her to read when she finally opened her eyes.

SensualSadist -- Good Girl. I am proud of you. You did well. Now. Sit there with that dildo in your ass while I ask you some questions.

It was several more minutes before she opened her eyes and read the message. She leaned forward carefully and typed.

Newandwilling -- Yes Sir.

SensualSadist -- Were you able to cum just from the anal fuck with the dildo?

She was slow to answer. He wasn't sure if it was because she was still zoned out or whether she was reluctant to answer.

Newandwilling -- Not really Sir. I fantasized a little.

SensualSadist -- What did you fantasize about?

Newandwilling -- I was replaying a video I recently watched.

SensualSadist -- What was happening in the video.

Newandwilling -- The woman was being forcibly held down and a large group of men were gang raping her ass.

SensualSadist -- And that allowed you to orgasm.

Newandwilling -- Yes Sir.

SensualSadist -- Do you want to experience a forcible gang rape like that.

Newandwilling -- I fantasize about it. Sometimes I think I would like to try it.

SensualSadist -- That is pretty extreme. Are you sure that you would like it?

Tony saw her smile just a bit at his question before she typed her answer back.

Newandwilling -- How would I know unless I try it.

Tony paused for a moment. That pretty much made him sure of his suspicions. He returned to the keyboard.

SensualSadist -- Take that dildo out of your ass. I want to just sit with you for a few minutes while you recover. If I were there, I would hold you and caress you softly. I would also turn you over and make sure that there was no damage to your rosebud asshole. The most important thing is I would be there with you to make sure you were safe and sound.

Newandwilling -- That would be so wonderful. I do enjoy cuddling. I love being held and caressed, especially after sex. Maybe I could entice you to fuck me again.

SensualSadist -- You are a lusty little brat. You just might make that happen.

They chatted mostly about nothing for the next few minutes. Then Tony saw Sasha look at the clock on the computer.

Newandwilling -- Sir. I hate to run away, but I have chores to do. I must run.

SensualSadist -- No problem. I understand. Thank you for offering yourself to me today. It was wonderful and you are wonderful.

He saw Sasha smile. It was one of her famous wide toothy smiles.

Newandwilling -- Thank you Sir. You have taught me so much. This is so much more enjoyable than FatherDom and his bunch.

Her name disappeared from the user list. Tony flipped over to the monitor app and saw that she had, indeed, closed down the laptop and disconnected from the internet. He pushed his laptop away and looked down at his lap. A large wet stain was visible.

Fuck me! Not again. I got to start wearing underwear with these thin pants.

&&&&&

Tony worked around his office most of the day. He spent more time reading, but he was now a little bored with the study. He was now seeing the same information over and over. His knowledge of BDSM and its associated lifestyle was in-depth. He had a wealth of book knowledge, but very little practical experience. That began to worry him so he called Angela, who had become his go to source when he was having issues or questions to which he could not find a satisfactory answer.

What he had heard from her gave him some relief. She had explained that while he was very short on practical experience, so was Sasha. If what Sasha told him was true and she had not taken her experience real time with anyone, she was no more experienced than he was. When he mentioned that she was now visiting his room exclusively on the chatroom, she seemed a little concerned. He couldn't see her logic until she asked what he would do if she suddenly came and asked him to accept her submission and wanted a collar. By his own terms, that would mean she wanted to escalate their online arrangement to a real time arrangement. If he declined, it could destroy her fragile world and push her the wrong way. If he accepted, he would have to make good on his offer. That would require him to meet her face to face which could destroy the illusion he had created. Suddenly, Tony felt like he had created a no-win situation. He spent a lot of time that day thinking about that.

Later that afternoon, bored with reading more of the same stuff about BDSM and dominants and lifestyles, He decided to take a drive and visit some of his websites. Some of the staff had already left. He grabbed his things and headed out to the parking lot. He knew where he had parked his truck, but it wasn't in its place. He looked around confused. He couldn't imagine that someone had the audacity to steal the truck right off the lot.

He turned back into the office when Dimitri and most of the rest of the staff came around the corner of the building.

"Did you lose something?"

"Yeah. My truck. Did someone move it or use it today?"

Dimitri smiled and he walked forward.

"Yeah. I told Charlie to take it back to the shop and have it serviced."

"Oh. ok. Are they still working on it."

"I think so. If you are ready to go, why don't you take this one."

Dimitri tossed a set of keys. Tony caught them and looked at the keys. They were unfamiliar and didn't look like any keys to any of the other company vehicles. Then the office staff separated and the black BMW that had been sitting behind them came into view.

"It's all yours. The leasing company delivered it this morning. We moved your personal stuff to it. It is all in the trunk."

Tony stood dumbfounded with a look of total shock and surprise on his face. He slowly walked forward looking at the car. He looked at the key and pressed a button. The lights flashed and he heard the slight movement of the locks. Opening the door, the waft of new car smell and leather was pleasant. He looked at his father-in-law and then shut the car door. He took a deep breath.

"Let's all go back inside. We need to talk."

Everyone headed back and gathered in the conference room. It was still a tight fit for everyone, since some of the job crews had shown up and wanted to get in on the celebration. It seemed everyone in the company except Tony knew about the car.

"I am overwhelmed at this surprise, but it may have to go back. I found out late today that the contract that I have been working on that required me to spend all these weeks studying and preparing for has been canceled. I can tell you what I know now. This was a military project. It wasn't top secret, but it was very closely monitored. Unfortunately, the Pentagon killed the project just as it was set to go. I don't know if I should take this car or not."

Dimitri laughed and everyone looked at him in surprise.

"Tony. Your phantom project didn't figure into this at all. This company has grown over 27 percent in the last 6 months. That's based on real numbers from real jobs, not some pie in the sky deal that the government offered. So, you got some new certifications. They will look good on your resume. That car reflects the current situation. Go drive it. You have earned it."

Everyone agreed and they all urged Tony not to let the disappointment of one failed contract get him down. He tried to respond positively.

"Dimitri, if you say so. I think I'm going home to show off my new car."

Everyone cheered and he headed out, climbed in the BMW and left the parking lot.

&&&&&

Sasha was standing in the living room, watching the kids play in front of the television when she saw a vehicle turn down the driveway from the paved road. It was long, sleek and black. She couldn't see who was driving but it was an unfamiliar car. It came down the driveway like it was on a mission. Sasha was a little alarmed as she realized the car wasn't stopping but continuing on around to the back of the house. She hurried to the back door and locked it then looked through the window.

The car came around the corner and pulled into the spot where Anthony usually parked his truck. She watched apprehensively as the door opened and then she recognized Anthony getting out of the car. Her eyes opened wide, and she hurried to the backdoor and ran out onto the deck.

"What in the world? Where is your truck?"

He grinned at her from the bottom of the steps.

"The truck is in the yard at the office. Come down and check out our new ride."

She hurried down the steps. Tony was opening the doors of the BMW and standing like a kid at Christmas.

"Come look. It has all the options and accessories. It goes like a bat out of hell, and it is like riding in a dream."

Just then the kids, having heard their dad's voice, came bounding down the stairs and stopped wide-eyed.

"Come on. Get in. Let's all go for a ride."

He took them on a long ride down some of the back country roads, then out on the superhighway. Everyone was excited, asking questions, and testing out all the features on the car. Tony showed them the impressive information system and then how the car could use his phone to make and receive phone calls.

Almost two hours later, Sasha finally looked at him.

"Anthony. We better get back home and have dinner."

"Don't worry about it. We are going out to celebrate."

He parked the BMW in the lot next to their favorite pizza place. Inside the kids were off and away to play games, ride the rides, and watch the animated show that was the feature of the place. Tony and Sasha ordered pizza, salads, beer for themselves, and sodas for the kids.

Sitting at a table watching the kids running and screaming in delight, Sasha looked at Tony. He was focused on watching the kids play. Her mind was elsewhere.

He's changed in the last few months. Not just the clothes and the car. He seems more intense, more in control. I don't know exactly what it is.

She reached over and laid her hand on his forearm. He glanced over at her with a faint smile that set her heart fluttering. It was the first time in a long time that she had felt that sort of thing just looking at him. It was a good feeling. The pizza arrived and Tony called the kids back to the table. The rest of the evening was a blur of pizza, beer, and games.

&&&&&

After he told the staff that the project, he had been working on had fallen through, his workday changed a little. He still got to the office early, usually before anyone else. He would stay closed up until noon but then he would appear to chat with everyone. He was again actively working with clients on contracts and tried to schedule all of his client meetings for the afternoons. He resumed his habit of visiting a different job site late, after everyone had left for the day before he started home in the evening.

Dimitri had the organization headed in the right direction. Tony met the new employees and was impressed with Dimitri's choices. Dimitri had also told him that they were adding two new contract specialists that would do most of the dealing with their clients after the contracts were signed. That would free Tony up to deal with new clients or old clients with whom they needed to remain in contact. Tony found the new role much to his liking. It left him with plenty of time to attend to his special project.

His mornings were still spent closed up in his office with his laptop. He continued to study and explore, but now he was expanding this to include a wider variety of the fetish and kink world. He was learning rapidly about how deviant and perverse some people could be. Some of them he found erotic, some of them just disgusting, but all of it interesting.

He continued to carry on the interactions with Sasha as SensualSadist. True to her word, she was in the private room every morning. He found teaching her was almost as much fun as playing with her. He enjoyed expanding her knowledge of the BDSM lifestyle. She was an eager student and willing to learn.

At first, he was not quite as adept at doing online play as he had first thought. It required a lot of thought and planning on his part to ensure that the scenes were organized and kept expanding her horizons and pushing her limits. As he waited for her to appear that morning, he was thinking back about how he had changed his methods over the last few weeks.

At first, he had relied on what he had seen watching FatherDom deal with her. He soon realized that he had to find a more sustainable way to give her what she needed as well as branch it out to push her limits. He relied a lot on what he knew of her video watching habits. She was not spending as much time as she had previously watched the pornographic BDSM movies. He took that as a good sign that what he was doing was keeping her somewhat satisfied.

He based a lot of his own play with her on what he knew she was watching. If she was finding the subject matters of the videos arousing, he decided to play into that. She even mentioned at one point that he seemed to have a knack for knowing exactly what she was thinking about and wanting. In the past few weeks, he had commanded her to do such things as whip her own ass with a leather belt, to wind her breasts with rope very tightly. One time he even had her hog tied herself. It was arousing and erotic.

Today, he had some special things in mind. He went to get a fresh cup of coffee and when he got back to his desk, she was in the room.

&&&&&

SensualSadist -- Good Morning

Newandwilling -- Hello Sir

SensualSadist -- Are you ready to try something a little different?

Newandwilling -- Yes Sir, always!

SensualSadist - First, I want you to share your computer with me. I will send you a link to set up the remote share utility.

Newandwilling -- Yes Sir.

Tony pasted the link to the remote utility and waited. In a few seconds he saw the prompt on his computer, and he saw her screen show up in a window on his computer.

SensualSadist -- Now go to this link and create an account.

He pasted another link and watched her screen as she followed the link, and the website came up. He saw what she saw. Sasha was now looking at the splash screen for a website called Different Strokes. It was a website that offered live adult unmoderated video chats with women. There were any number of categories. He began to give her directions.

SensualSadist -- I want you to set up a presenter account. Click that button on the menu.

She clicked the icon. The registration screen came up. It required that she fill in a bunch of personal information. She hesitated, not wanting to give up such personal information, especially since he could now see her screen.

SensualSadist -- Don't worry. I can't see this part of the screen. If you want to stop the remote utility you can do so and when you have finished the registration, turn it back on.

His view of her computer went dark. He was glad to see that she was trying to preserve her identity at least to this extent.

Sasha was a little uncomfortable at this point. She wasn't exactly sure what he had up his sleeve. The request for her to share her screen was different but she complied. After she filled out the registration form, she clicked continue, and came to a screen asking for her credit card information. She stopped. Sasha wasn't sure she should take this step. Then she read that the credit card was not for her to pay for anything, but it was a way for the website to send any money she generated back to her. She found her credit card and put in the information and hit continue. The last screen was a disclaimer and a release. She skipped through it hurriedly and clicked again. She had to do an email validation which took several minutes and then she was on the website under the same username she used on the chat site. She clicked to resume sharing her computer.

Newandwilling -- All done Sir.

SensualSadist -- Good girl. Now we need to create a room. Click on create a room and I will tell you what I want you to put in.

She clicked the link and was presented with another signup screen. This one appeared to have a bunch of options to select. She followed the directions he sent. He told her to click on the category and to pick BDSM from the list. The next option was to set the level and he told her to click 10, the most extreme level available. He had her scroll down and select an option that allowed multiple users to be in her room at once. The last selection was to set the room to pay per view only. Once those were completed, she found herself looking at a screen similar to the chatroom screen. Most of the screen was blank. On the right side a narrow vertical bar titled Users ran along the border of the screen. She saw that chatroom icon blinking and she opened it to see a new message from him.

SensualSadist -- Here are your instructions. First, get on your couch and set the laptop on the table where it can see all of you when you are on the couch. I want you to strip completely and sit on the couch facing the camera. Get the toys that you have and keep them in reach. People will come into the room. You can chat with them, but these men are paying money to see you naked and to see you perform for them. For the next two hours you will do what your customers request.

Sasha gasped when she realized what he had set up. She couldn't believe that he was going to have her perform live sex shows. She was considering using her safe word when the first name popped onto her list. She saw the user "Popeye" and immediately saw his request come across the bottom of the screen.

Popeye -- My, you are beautiful, and you have luscious tits. Can I get a better view of them?"

Not quite sure what to do, Sasha leaned toward the camera to give a closer view of her breasts. She saw another message come across.

Popeye -- wonderful. Do you have nipple clamps?

Sasha didn't reply. She held up the cloverleaf clamps for the camera and then, for some reason, smiled provocatively.

Popeye -- Excellent, put them on

Sasha opened the clamps and gingerly placed them on her nipples. She rubbed her hand over her breasts and groaned slightly. She looked to see that there were now 8 names in her user list, and she was getting messages from all of them. The thought that she was visible to all these men sent her arousal level up several notches. He read the requests. She answered some of the questions and when asked to perform, she did so, willingly and enthusiastically.

Tony watched the window that showed her screen. He was also watching the video feed from her camera which was what the men in the room were seeing. He saw her put on the nipple clamps and then caress her own breasts. She leaned back on the couch and spread her legs when one of the men asked to get a better view of her pussy. It wasn't long until she was on her knees on the couch with her ass toward the camera, working the long butt plug in and out of her ass. Tony could see her large breasts hanging down beneath her swinging and swaying as she pumped the cock shaped butt plug in and out of her asshole.