Lisa's Predicament

This is going to be a long series so please be patient with the slow start. There is not much sexual content in this chapter but it should pick up soon. Please feel free to share your thoughts and all feedback is welcomed.

All characters are of legal age in this story.

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On the surface, Lisa was a successful 34 year old woman. She was known as a hard-worker and that had vaulted her into the position of becoming a VP at her boutique firm. She oversaw a majority of the employees, most of whom were located at her local office. Her immediate supervisor, the CEO, had left most of the day-to-day responsibilities to her while he focused on the big-picture stuff, as CEOs tend to do.

But no one knew about the internal struggle Lisa faced daily. She was a high charged VP who lived a double life. Due to her struggles growing up, she had suffered a lot of damage to her psyche. In spite of being a successful business woman who almost always took charge of meeting, Lisa had a very submissive personality. She tried very hard to keep it hidden, lest in come in the way of her success. And she had done a very good job at it, moving up through the ranks at her job.

She had kept her submissive desires for a long time, burying herself at work. She knew that if she let that side of her out again, it would ruin her completely. But that gave her a weird high too, knowing how she could lose it all in the blink of an eye.

Lisa always worked late at night and had no social life. Due to her past, she did not have any friends and because of her long working hours, she did not have the time or the desire to make new friends. The truth was that Lisa did not enjoy having a traditional relationship, whether platonic or romantic.

Her past had permanently changed her vision of relationships and she knew she could only enjoy the abusive kind. Therefore whenever she could, she would go home at night and log into anonymous chat rooms to chat with Doms. She felt that would let her explore her submissive side, without getting in the way of her job. She had always struggled for money and so worked this hard but the ironic fact was that all the money and success did not give her a sense of fulfillment. She still felt like she was missing something and that is what she sought after in those chat rooms.

This night she got home late, poured herself a glass of wine and settled down in her home-office before logging onto the chat.

It was the usual flood of responses asking for ASL, pics, etc. She did not want to prove to anyone that she was actually who she was so most of these messages bothered her. Most men there were just looking for pics to jerk off to.

As she was idly browsing around, she got a message from someone named "Dom_Humiliator". Just seeing that name got her curious. The message was not a typical ASL or anything on those lines. It simply read, "What kind of panties are you wearing slut?"

Just reading that message sent a tingle down her spine and she decided, what the heck, why not chat. She found a strange exhilarance from sharing the kind of panties she was wearing.

This "relationship" of Lisa's got steadier over time. She would talk dirty to this person and he would talk about ways of humiliating her. He would even make her rub herself to some well earned orgasms. It was like she had her own online Dom/buddy and she began to feel very comfortable around him.

He had never asked her for a picture or even asked for her age. One day as they were chatting, as usual he asked her for the kind of panties she was wearing but this time he wanted a picture. She thought about it for a second but thought, nothing wrong with that and so took a quick upskirt pic and sent it to him. That was the beginning of the next phase of their relationship.

One day he asked her if she wanted him to dress her for work. She thought it would be fun to have a complete stranger picking her underwear and work clothes. It would be kinky. So she took pictures of her closet, all her clothes, her underwear and sent it to DM, as she referred to her Dom.

DM began to dress up Lisa almost every day, sending her a message every morning on what to wear. Lisa got a huge rush out of the fact that in spite of being a VP, a stranger, somewhere in the world, knew the most intimate details about her. As a matter of fact, he was the one deciding what she was going to wear.

One day, he asked her to take a full body picture of the way she was dressed and send it to him. She thought for a minute but figured that was asking for too much. She refused him the pic and DM was furious. They did not talk for a few days and Lisa was plain miserable. She could not stop thinking about him. She hated the fact that she was picking her own clothes and there was no one to boss her around. She figured she would get over it with time but it just made her miss DM even more.

Finally one day she gave in, dressed the way DM had last wanted her to be dressed and took a full body pic and sent it to him, covering her face of course. She immediately got a message back from DM saying that wasnt good enough and that he actually wanted to see her in her underwear. This was a form of punishment since she had been such a bitch to him. She pondered it over again but could not bear the thought of not chatting with DM again, so she simply stripped to her underwear and resent him the picture. She simply got a thumbsup emoji back from him but that was enough to keep her elated through the rest of the day.

The next day she got a message from DM in the chat, asking her to make time for a long chat. That they needed to talk to discuss their future. She was nervous because she did not know what to expect from him. She really did not want to lose him but was afraid what he would ask of her.

She logged onto the chat that night and waited for DM to log in...