Lisa's Predicament Ch. 02

This is going to be a long series so please be patient. Please feel free to share your thoughts and all feedback is welcomed.

It would be helpful to read the first part to get some background on Lisa.

All characters are of legal age in this story.

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Lisa sat in her home office, fidgeting in front of her computer, waiting for DM to log in. As soon as she had come home, she had poured herself a stiff drink and had parked herself in the office. She kept wondering to herself, what did DM want? What did he want to discuss with her? Was he upset? The questions kept coming like a tsunami. She had not felt this much at unease in a long time. Lisa had been in meeting with very rich and powerful people and had always been very sure of herself but this was a feeling she had not felt in a long time. It made her uncomfortable, yet was exhilarating.

Finally DM logged in and Lisa's heart skipped a beat. She immediately messaged him and waited impatiently for him to reply. He finally replied, "So how is the haughty bitch doing?"

She meekly replied, "I am fine, thank you."

Lisa could not see it but DM had a wicked smile on his face and he knew he had hit the lottery with this girl if he played his cards right. He had big plans for her and he had an inkling that with the right approach, he would be able to bend her to his will.

"I am bored with what we have been doing and I need to know if you are in this for real or if this is just a game for you."

Lisa had a huge lump in her throat and knew that this was getting close to being decision time for her. She had worked very hard for a long time to get away from her past and now she had gone seeking something similar to that again.

She had not felt this level of excitement in her life in a long time but at the same time knew that if she moved forward with DM, she would have a large price to pay. Was she willing to pay that price?

With trembling fingers she wrote back, "Yes I am in this for real and would like to move forward with you. I have not felt this way in a long time and want to continue being yours".

DM smiled to himself and wrote back, "Well, in that case, strip to your bra and panties and turn on your webcam. I need to see the whore whose life I am going to control."

Lisa swallowed hard and turned on her webcam. DM did not have his on so she could only see herself on the screen. The gravity of what she was about to do was hitting her like a ton of bricks.

Lisa Williams, the powerful business executive, was about to strip to her underwear in front of a cam for a man that she did not know was how old, where he lived, his real name or anything of substance. He was just a ghost to her and here she was, making herself so vulnerable to him.

She did as told and was just about to sit back on the chair when a voice boomed from her speakers, "Did I tell you to sit slut?"

Even though DM was not on cam, she had finally heard his voice for the first time. She was startled for a second but was able to gather her wits about herself.

She stood meekly by her desk, looking at herself on the screen with her arms folded across her 34d boobs enclosed in a lacy black bra and her matching black thong on.

"Do you want me to control all aspects of your life slut? You know that is the only way I am going to be interested in you. You know that you do not deserve all this wealth and success you have had and that you are tired of pretending you like all of this. I am going to take over your life and fucking destroy you. That is what you want, isn't it my whore?"

Hearing him talk so crudely was making Lisa unbelievably wet. It was like he was inside her head and knew her most intimate thoughts. The truth was that Lisa had worked so hard to get away from what she thought was a bad situation but in reality it had not given her any kind of happiness over time.

With her rapid success at work, she had been rewarded very handsomely. She had all the material comforts that money could buy but was still miserable. She hated dating because she found out over time that all the romance that came with dating was mind numbing to her and that she hated it. She hated when she was praised or applauded for because she felt like an imposter. She had been to shrinks but they were of no use either. She just wanted to give up control and have someone else make the decisions for her.

She snapped back to reality and said, "Yes, I want you to control all parts of my life and be in charge of everything. I need you to do it."

Just saying it out aloud was enough to make her cream her thong a little more. She could feel them being completely soaked. This was something she had not experienced in a long time and was enough evidence to herself that the path she was choosing was the right one for her.

For the first time she heard DM chuckle and say, "Of course that was the answer. Now I want you to tell me about your house and then walk me through the house so I know what I am dealing with. Take the laptop with you and describe each room to me."

Lisa picked up the laptop and started walking through her 5 bedroom house in her underwear, showing it off to this complete stranger. She had thought that her buying a mansion would fill a hole in her life after coming from an abusive mother living in a trailer but it hadn't. She was just as miserable, if not more and hopefully this new direction in her life would be more fulfilling.

DM was astounded to see the house as Lisa walked around it. He was of course recording everything and knew that he would put it to good use. His gut feeling of this being a great thing was turning out to be real and he could not contain his glee. This stupid woman was living by herself in a 5 bedroom house and was going to give him all the control of it.

Once done with the tour, DM admonished her.

"So much space for 1 whore? Such a waste of resources. You should be ashamed of yourself Lisa."

And she knew he was right. She was ashamed of it all. Again, that imposter syndrome kicked in and her face turned red.

"Not to worry, it will all be sorted soon enough."

"Now sit down and let me give you your next task."

For the next 15 minutes Lisa listened to DM explaining her next task to her and with each word she heard, her face kept turning red. Finally DM disconnected and instructed Lisa to get to her task.

Lisa slowly got up and made her way to her bedroom, still wearing just her bra and panties. She looked through her closet and picked one of her best looking skirt suits. She put on the sharp black suit with the white blouse, did her makeup again and looked in the mirror. She looked ready to go to work and kick some serious ass but the truth could not be any further!

She called in for an Uber, took one last look at herself, pumped herself up quietly and made her way down to wait for her ride. When her ride finally arrived (it took a while because she lived in an almost rural area outside town), she got in, still unsure if she should go through her task. As they drove away, she knew that she would have to follow through on the task or she would lose DM for ever. She knew he was not bluffing and did not think would get another chance with him.

After what seemed like an eternity, they finally pulled up to a bar in a part of town frequented by business travelers. It was the hotel district and at this late hour was peppered with out of towners passing away the time.

Lisa carefully made her way to the bar and perched herself on a bar-stool. She did not necessarily stick out the way she was dressed. In fact, she fit right in. Soon enough she started getting approached by these well-dressed men asking if they could buy her a drink but she kept turning them down. Her instructions were clear and they did not meet their criteria. She ordered herself a scotch, to calm her nerves and also to nurse so that she could continue scoping out someone who would satisfy DM's requirements.

After a while, she noticed this guy sitting at the other end of the bar striking out for what was at least the fifth time that night. While most of the men were dressed in business casual or just formal wear, this guy was wearing a suit. He had blonde hair in a pony tail, a slight stubble, scrawny looking physique covered with a cheap suit. Coming from her world she could spot a cheap off the rack suit from a mile away and this guy was trying his best to rock one. All the women that had turned him down were not quite as good looking as her and she knew that with this fact coupled with his appearance, made him the ideal candidate.

She got up and walked over to his side and sat on the stool next to him. Right on cue Mr. Ponytail perked up and asked her if he could buy her a drink. She gulped down the remainder of her scotch, put on the brightest smile and told him of course.

Mr. Ponytail could not believe his luck and immediately flagged over the bartender and asked him to refill her drink. He introduced himself as an out of town salesman for copiers. Lisa did not even know that was still a thing and thought how appropriate it was. It was like the job fit his personality to a tee.

Lisa of coursed feigned interest and appeared to be very impressed with him and they began making small talk with her asking him all kinds of inane questions and him answering them enthusiastically. Obviously soon enough he asked her what did she do for a living. And this was the first point of hurdle for Lisa and she knew that it was definitely now or never.

She again put on her prettiest smile and told him that she was a secretary for a small local business. As she said, she twirled her hair in a girly way as she said it but deep inside, she had a pit in her stomach. Here she was, a senior VP, introducing herself as a secretary, much less in a bimbo way.

Mr. Ponytail was of course very impressed by that and started making comments about how that was his guess as well, especially based on how she was dressed. That came across as a gut punch to Lisa because she usually dressed in this fashion and with being a senior VP, it was expected of her. Instead this loser thought she was a secretary and that it was of course expected.

The sexist comment came across as a gut punch but also gave her this weird kick. Immediately Mr. Ponytail could not be bothered with hiding his sexist feelings. He told Lisa a couple of very sexist jokes and Lisa laughed along very heartily to them, encouraging more of this behavior.

This is what DM wanted from her. To have a casual encounter with a sexist and possibly racist man to humiliate her. He wanted to play on her Latina heritage and demean her even more. Of course he did not care that she was only half latina from her mother's side but he was going to use this to degrade and humiliate her from now onwards.

She finished her second drink very quickly as she was getting increasingly nervous. As she gulped it down, Mr. Ponytail ordered her another one without even waiting for an answer from her. She did not object to it because she would need all the liquid coverage she could get to get through the night.

As the third drink got poured, his hands were now on her thighs as her skirt had slightly risen up. She did not make any effort to pull it down and did not object to his hands either. She had to admit that even though he was not the best looking guy, he was pretty ballsy with his moves. She was positive that with her letting her guard down, he was going to get more aggressive with his approach.

As she started on her third drink, his hand was half way up her thigh and slowly pushing her skirt up. He was certainly getting braver and possibly seeing what he could get away with. Seeing no objections from her they continued to inch upwards. Thankfully she was facing away from the rest of the bar so only he had a view of her front side.

As she slammed down her third drink she was definitely getting tipsy having not eaten. She leaned towards him, told him how sexy he was and started kissing him. Mr. Ponytail did not need to told twice and soon enough he had covered him in a tight embrace as their tongues intertwined.

Lisa could not believe she was making out with a sketchy looking man in a bar like this but the liquid courage was definitely helping her. As they broke their kiss, he grabbed her hand and told her lets get out of here. As he was fumbling for his card to pay, she threw down a bunch of cash on the counter, kissed him again and told him lets go.

Lisa could not believe that she was leaving the bar with this man but at this point in time she had stopped caring. He told her that his hotel was not too far and as they walked, his hand was firmly on her ass. They walked past a couple of hotels and as they approached a Super 8, she began to pray that they would walk past it but as luck would have it, that is where Mr Hotshot Ponytail was staying.

Of course Lisa acted all impressed that they were in a Super 8 and kept cuddling with him as they walked. When they finally entered the room, he threw open the light switch and they began to furiously kiss. Lisa was almost having an out of body experience because she had not been this way in a long time. Just acting like an animal in heat. She finally remembered what it felt like and all the skepticism went right out the window.

In a flash she was on her knees and had pulled his dick out. It was an average looking dick but it felt like the best dick in the world at the moment. He had not expected that from her but he had his hands running through her hair as she took him in her mouth.

He had not had a blow job in a long time, much less from a beauty like this one. He made her take off her jacket and did not hesitate to push his hands in her blouse getting a grab of those boobs at last. He began to knead them roughly as Lisa continued sucking on his cock. He felt like he was in heaven and did not want to stop but all of a sudden she pulled his cock out and stood up.

Lisa took off her skirt in a flash, got on her knees on the bed and pulled her panties to the side. He did not need to be told what needed to be done and he got on the bed and plunged right into her.

Lisa was soaking wet and he slid right into her without much difficulty. Just feeling the cheap bedsheet on her face, getting mounted by this absolute stranger bareback gave Lisa second life and started screaming in a deep guttural voice as Mr. Ponytail fucked her from behind. Very predictably he did not last very long and came right in her pussy. Even though Lisa had not cum yet, just this encounter had gotten her so horny and worked up that she did not care about it.

She was just proud that she had been to use her body to make a man empty his balls into her. None of the money and power bullshit. Just a man and a slut.

As he pulled out, Lisa turned around very dutifully and took his cock in her mouth once again to clean him up. Once she was certain that he was clean she let out his cock from her mouth.

Mr Ponytail did not care one bit about Lisa's pleasure and simply walked away to get dressed. As Lisa pulled her panties back in place and put the bra over her boobs, she told him how fantastic he had been and that he had given her so much pleasure. It was not the total truth as she had not cum but just getting him to cum had been incredibly powerful to him. As she lay on the bed in her underwear and he got dressed she basked in this glory that she felt. She saw her skirt, blouse and jacket strewn across the floor and it just felt very appropriate that they were there and she was in bed of this stranger in her underwear.

She asked Mr. Ponytail if she could spend the night with him and he didn't seem to care. He fell asleep soon enough and the alcohol made Lisa nod off too.

Lisa woke up in the morning and Mr Ponytail was still sleeping. Now it is time for the last part of DM's task. She very quietly made her way to the bathroom and was immediately disgusted by how nasty it was. She had never stayed in a Super 8 before but this was not what she expected. Still she felt like this is what she deserved and nothing more. She did not deserve her large house or the big bank balance. She deserved to be fucked in cheap hotels by strangers.

She finished her business and walked back out into the room. He was still sleeping and her suit was still laying on the dirty carpet. She could not believe she had knelt on that nasty surface. She quietly got dressed and left without making much noise.

Her Uber was already outside waiting for her and took her to her office. This is what DM had wanted. For her to get fucked by some misfit stranger, to spend the night with him and then go straight to work without a shower or change of clothes. He wanted her to feel dirty and nasty at what she considered to be her place of excellence and to think about how much she missed being treated this way.

Sure enough, as she sat in her office contemplating the last 24 hours, typing up her notes to send to DM, that is exactly how she felt. She was glad she had not chickened out and was wondering what he would make her do next. Would he degrade her even more?

To be continued...