To Catch a Sub - 009

To Catch a Sub - 009

Sasha was up and smiling as she got the kids off to school, did some laundry and a few other chores around the house. She got the laptop out and settled down with a cup of coffee. For the first time in a long time, she wasn't feeling a driving need to go find something to help her get her sexual needs fulfilled. She was looking forward to talking more with SensualSadist. He seemed to her to be articulate and carrying. He obviously had a much more in depth understanding of BDSM and a whole different philosophy than the others she had met in the chatroom. It seemed to satisfy her in ways that the uncaring dehumanized sex that had happened so far was able to do.

The laptop came to life, and she clicked on the chatroom link. She immediately types in SadisticPleasures and finds herself in the room. SensualSadist was already there and messaged her quickly.

SensualSadist -- Good morning! I'm glad you made it.

Newandwilling -- Hi! I have been looking forward to talking to you again. I learned so much yesterday.

SensualSadist -- That's good. I have been thinking about you as well.

Newandwilling -- Oh?

SensualSadist -- Yes, on several levels. I am a little concerned about your nipples and breasts. How are they doing?

Newandwilling -- It is sore and tender, but I don't think there was any real damage. Thank you for asking.

SensualSadist -- That's good. Keep an eye on it. If you want me to keep an eye on it, send me a pic.

Newandwilling -- LOL. Haven't you seen enough?

SensualSadist -- You are a very sexy and beautiful woman. I don't know that I could ever get enough of looking at you.

Newandwilling -- You are a flatterer Sir.

SensualSadist -- I deal in the truth and that is how I see it. The dominant who finally catches your eye will be a lucky one.

Newandwilling -- Who ever said I was looking for one?

SensualSadist -- My experience tells me that if you weren't looking you wouldn't be on this website.

Newandwilling -- I am pretty happy where I am.

SensualSadist -- You married?

Newandwilling -- Yes.

SensualSadist -- But he doesn't give you what you want?

Newandwilling -- I love him dearly and I don't want to leave him. I am just needing something more than he seems to understand.

SensualSadist -- What is it that you aren't getting?

Newandwilling -- It's hard to explain. He is a good lover. He satisfies me for the most part. But I have found the videos and the other stuff, and they turn me on so much. I want to experience that.

SensualSadist -- So, instead of talking to hubby, you go and find your solutions online.

Newandwilling -- it does sound a lot like cheating, doesn't it.

SensualSadist -- It could be a big trust issue.

Newandwilling -- I know. And I think about that constantly. I don't want to deceive him. I don't want to cheat on him. But I just can't bring myself to admit to him that I am such a deviant and a pervert.

SensualSadist. -- What if you found out he is just as bent and twisted sexually as you are.

Newandwilling -- I doubt that is true. He is such a sweet guy. I just can't see him being like that.

SensualSadist -- Really. He hasn't ever given you any sense that he might find this interesting.

Newandwilling -- Now that you mention it. He did tie me up the other night on sort of a dare. It was fun... a little awkward since he wasn't really very experienced.

SensualSadist -- Did he seem to enjoy it?

Newandwilling -- I think so. He seemed to.

SensualSadist -- You need to really think about this. I came here tonight to offer you a chance to train with me online privately.

Newandwilling -- Really?

SensualSadist -- The caveat is that it is only an offer if you agree to do at least one real life meet as part of the training.

Newandwilling -- I see.

SensualSadist -- Think about it.

Newandwilling -- Can I ask what the training would consist of the online part I mean.

SensualSadist -- Of course. You will learn about what a real BDSM relationship is like, what is required, what to expect, and how it works. There would be exercises and tasks for you to do. There would be some online play much like what you have done with FatherDom.

Newandwilling -- What kind of timeline does this involve?

SensualSadist -- If you are online every day for at least a couple of hours, it would probably take no more than six weeks.

Newandwilling -- and then?

SensualSadist -- You would be expected to fulfill the obligation to spend 24 hours with me as my submissive. There is a chance that at the end of the 24 hours, if you wished to extend your gift to a full-time commitment, I would consider that.

Newandwilling -- Can I think about this?

SensualSadist -- Absolutely. No pressure. It is completely up to you.

Newandwilling -- Thank you Sir. I will think about it. I need to go now and take care of some chores.

"SensualSadist -- I will be here tomorrow. You can also message me through offline messaging system at #SensualSadist.

Newandwilling -- Thank you.

&&&&&

Tony leaned back at his desk and laced his hands behind his head. He wasn't sure if the tactic he had decided on was the correct one or not, but he believed that he had captured Sasha's attention and gotten her away from the sort of danger posed by online dregs such as FatherDom. He thought that perhaps getting her focused on his alter ego and perhaps even closely involved would lead to the opportunity to convert her affections back to his real personality.

One problem he was having was the necessity to keep up the charade of studying for the certification exams. It was beginning to wear thin, and he had to find something concrete to show for the time he had been spending stuffed away in his office. He didn't want to create something else out of thin air. He saw now that his choice to pretend to be doing this certification process to allow him to carry on with his project had some definite downsides.

He called Mark to have someone to talk to. When Mark answered, they planned to have a last lunch. He fiddled around the office doing some more reading. At one point he actually went back to the Pillory website and spent time looking at video offerings. He had made a list of the videos that Sasha had watched. He started working systematically through them, making notes about the content of the videos, the premise of the often-thin plots, and detailed notes on the action that he thought she was finding so attractive.

It was almost 2 pm when he closed the laptop and grabbed his coat. He shrugged on the sports coat and headed out to his truck. He had about 10 minutes to get to the restaurant where he had agreed to meet Mark. Mark was already there and when he came in, Mark looked up and then his eyes widened in surprise.

"Jesus. You look different."

"Thanks. New me...or at least on the road to the new me."

"What's going on that needs this impromptu engagement."

"I made a mistake with this project concept."

"You mean something has gone bad with Sasha?"

"No. no. I think that is still on track. But this charade of studying for certifications to get a project is wearing thin. I don't have anything to show for the time I have spent and no prospects to make it seem probable. I've got to come up with something quick. Otherwise, I have to somehow mitigate this farce.

Mark thought for a moment.

"What if the contract fell through?"

"Huh?"

"What if the people behind the contract had a financial implosion and can no longer do their project. It's not your fault, you just got caught in the fall out. You spent a lot of time and effort on what you thought was going to be a game changer, circumstances beyond your control made it come out otherwise."

"That's not bad. We lose contracts for a variety of reasons. I never told anyone it was a done deal."

"See. I think that could work."

"I need to do some thinking about this. I'm sure someone, probably my father--law is going to want details. I have to have something to give him."

Mark was silent for a minute.

"I worked last year on a security project for the military. They were looking at putting some kind of secure military installation here. It all went south when the new administration took over. Use that excuse. The military never discloses much, even to their contractors. It's not that unusual for them to start a project, hire contractors and let contracts and then walk in 6 months later and tell everyone to go home. They do it all the time with no explanations."

"That could work."

How are things otherwise?"

"Going as good as I could imagine I think."

"Good. Let's eat and have a beer. Did you see that game on Saturday? The refs screwed that up royally.

They continued to talk about sports, politics and business for the next hour and half. Mark looked at his phone.

"I got to get along. I have to relieve the other guy in about an hour and I need to pick up some stuff."

"Like what?"

"Oh hell. Coffee, snacks, water bottles, magazines. It's a long night and I don't expect much to happen. This guy's wife thinks he is having an affair. The only thing he is making love to is a bottle of vodka. A total raving alcoholic who gets shit-faced hammered every night and ends up sleeping it off in the back seat of his car. A total fucking loser."

They went their separate ways. Tony looked at his phone and saw that he had several hours to kill before he was due home. He decided to do something he hadn't done in a long time. He drove to several of his job sites to look around and see how things were going.

&&&&&

After dinner that night, the kids were down for the evening. Tony was down in the garage basement looking around. He had an idea for the enclosed basement space, but he wasn't sure exactly how to proceed with it. He was studying the way the ceiling joists and framing above the space had been built and calculating how much square footage would be usable with the enclosed area. He had to do some more research on what would be needed for the space he wanted to create.

He heard the upper door close and saw Sasha coming down the stairs.

"What are you doing down here?"

"Looking around. Planning. Thinking."

"And?"

"I'm not sure yet. I have a vague idea but nothing worth talking about now."

"Are you coming upstairs soon?"

"Right now. You got something you want to do."

"Oh. no... just sort of wanting to be with you."

He walked up behind her and slipped an arm around her waist from behind. She leaned her head against his chest.

"Let's go upstairs. You can get naked, and we can play spank and tickle."

She started to grin and then the thought of her badly bruised nipple caused her to stop.

"Not tonight. I'm tired. Let's just go to bed and snuggle."

He frowned a little but recovered.

"Absolutely."

They headed upstairs holding hands.

&&&&&

The next couple of days seemed almost routine. Tony got to the office early as usual and made coffee. He spent most of the early morning hours reading. His knowledge of the subtleties of the BDSM lifestyle were becoming deeper and more understanding the more he learned from the people Angela had pointed him toward. Just before he knew Sasha was due to arrive, he opened the screen with his private chat room and waited. He was soon rewarded when she popped into the user list.

Newandwilling -- Good Morning Sir.

SensualSadist -- Good morning. How are you this morning?

Newandwilling -- I'm doing well. What is in store for this morning's lesson?

Tony knew from the monitor software that she had been visiting the video site regularly since she had been talking to SensualSadist. It appeared she was satiating her desires with the videos. Rather than playing in the chatroom. He had decided that he needed to take things up a notch. After reviewing the videos, she had been watching over the past week or so, he thought he was ready.

Sensual Dom -- Today, we put some of what we have been doing into practical application.

Sasha's heart skipped a beat. She typed back quickly.

Newandwilling -- What do I need to do Sir?

SensualSadist -- Be patient. We will get there. First, I want you to pick a safe word.

Newandwilling -- Shouldn't you give me my safe word?

SensualSadist -- No. It needs to be something you can remember no matter the situation but that you wouldn't normally utter in the course of being aroused and excited. It also shouldn't be a word like no, stop, quit, or don't. Those are words that you may use out of passion when you don't really want to stop. Often the word RED is used. It's a good indicator of a stop and it is easy to remember.

Newandwilling -- That will be good. I can remember that. RED

SensualSadist -- Good. Understand that if you say or type RED, everything stops right there.

Newandwilling -- Yes Sir

Tony knew from looking at the videos she had been streaming that most of them were anal focused. She had watched selections from a variety of categories, but they all seemed to center around anal sex of some sort. He decided to play on that with her.

SensualSadist -- Are you comfortable starting your video feed so I can see what you are doing.

Newandwilling -- I don't mind, Sir.

The screen flashed and the video window opened. He could see Sasha sitting on the couch in their living room holding the laptop on her knees and leaning back on the couch. She was wearing a t-shirt.

SensualSadist -- I want you to get that big dildo you ordered and a bottle of lubricant.

Newandwilling -- Do you want me to use the lard Sir?

SensualSadist -- Absolutely not. That is not sanitary. Do you have lube?"

Newandwilling -- Yes Sir, upstairs.

Sensual Sadist -- Go and get it with the dildo.

Tony watched as she put the laptop on the coffee table. He could see her walk behind the couch and disappear. In a few minutes she came back carrying the dildo and a squeeze tube of lubricant. She sat down on the edge of the couch.

SensualSadist -- Good girl. Now strip. Everything off

Tony watched closely. She didn't hesitate at all. She pulled the t-shirt over her head and then pulled the shorts down her legs and tossed them toward the end of the sofa. She sat back down on the edge of the couch and reached over to type. As she did, Tony had an unobstructed view of her pussy between her legs.

Newandwilling -- All done Sir.

SensualSadist -- So I see.

Tony saw her smile on the video as his words. It didn't seem to embarrass her at all.

Sensual Sadist -- Listen carefully to my instructions. I want you to move the laptop to the couch where you are sitting so it faces the coffee table. I want you to put a dab of lube on the suction cup on that dido and stick it on the coffee table. Put it about 6 inches back from the edge. Do it now."

Newandwilling -- Yes Sir.

The camera wobbled and jerked as she picked up the laptop and moved it to the couch cushion. He could then see her as she took the dildo, squirted a dab of lubricant onto the bottom of the suction cup. She pushed down on the dildo shaft until the lube oozed out of the edge. The dildo stood upright on the table, tightly stuck.

Newandwilling -- Is that suitable Sir.

SensualSadist -- Perfect. Now lube the head and shaft of the dildo.

Tony watched as she squirted a good amount of lube into her hand and then smeared it up and down the rubber cock as if she were stroking a real cock. She turned back and typed with one hand.

Newandwilling -- Done Sir.

SensualSadist -- Well done. Pay attention. Turn around and bend over. Make sure your asshole is visible in the camera. Squirt some of the lubricant in your asshole and smear some around your asshole.

He saw Sasha's eyes. She was not expecting that order. Sasha read the message and her mouth opened. She was expecting to be ordered to take the huge dildo into her pussy and fuck herself. She knew that wasn't too difficult. This, however, was a whole new ballgame. The dildo was at least three times as big as any of the toys she had put in her ass before. I had to be almost twice the size of Anthony's cock and she remembered what that had been like.

Slowly she turned and leaned over, sitting on her knees. She checked and saw that her asshole was centered squarely in the video screen and took up almost the whole space. She reached back and put the squirt tube at her asshole and squeezed. The thick gel spread over her asshole. She heard the screen ding and turned to read what he had written.

SensualSadist -- No. Stick that nozzle into your ass as far as it will go and squeeze that tube. Fill your ass with lube.

Sasha groaned. She fumbled a bit with the nozzle but finally got it in position and pushed. The thin plastic tube slipped into her ass easily. She pushed until the shoulder of the tube was against her asshole and she squeezed the tube as hard as she could. She felt the cold gel filling her ass. She also felt the cool wetness on her pussy lips. She pulled the tube from her ass and set it on the table and turned around to face the camera.

Tony watched as she filled her ass with the gel lube. He also saw the glint of moisture on her pussy lips. It caused him to smile just a bit to know she was getting turned on. When she was settled on her knees looking at the screen he typed again.

SensualSadist -- Good. Stand up and put yourself over that dildo. Your instructions are to fuck yourself in the ass with that dildo. You have to drive the entire length of it into your ass before you pull it out. You must then fuck your ass until you cum. You may not play with your pussy. You may not play with your clit. You can only cum be fucking your ass with that big dildo. Begin.

Sasha read the instructions. She was holding her breath by the time she finished. She looked back at the huge black dildo standing on the table, listening with lube. She slowly stood and positioned herself at the edge of the table and then her knees, leaning forward a bit to hold her balance until the head of the dildo was brushing her ass.

Tony watched. He could tell that she was not anticipating this task. When she was in position, she bent forward slightly causing her tits to hand down pendulously toward the camera. He could clearly see the bruise on her nipple. He watched as she slowly lowered herself until the cock was pressing on her ass.

Sasha felt the pressure of the cock head on her asshole. She lowered herself tentatively and she felt the pressure increase. It soon became almost unbearable. She pressed down a little more. Her ass stretched a few millimeters, and she felt a bit more of the cock widening her ass. It took her almost 5 minutes to work half of the monstrous dildo into her ass. She looked at the screen but there were still no words from SensualSadist.

Tony watched. From this angle he couldn't see the dildo enter her ass. He could see that she was struggling a bit to get it in. He let her continue to work as he watched. Suddenly her head came up. Her eyes were focused above the laptop and camera and she stared into infinity. He guessed that the head of the dildo had popped into her.

Sasha gritted her teeth and pushed down again. Suddenly the dildo moved more than she expected, and her anal sphincter contracted around the shaft of the cock under the head. She almost sighed in relief. She sank down another few inches and found the sensation of the huge cock stretching her almost enjoyable. She groaned slightly and continued to work the giant beast into her ass. It took her several minutes, but she felt the cool top of the table on her ass cheeks. The dildo was buried it full length in her ass. She opened her eyes and looked at the screen.

SensualSadist -- Good girl. Just sit there for a minute and enjoy that sensation. Remember, you may not touch your clit or your pussy. You must fuck yourself in the ass only until you cum.