Exploring the Lifestyle

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A lawyer leads a divorcee client in a new direction.
14.4k words
4.62
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32

Part 1 of the 3 part series

Updated 06/11/2023
Created 04/29/2013
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PART 1 THE INITIATION

Elizabeth had never met a man like Roger. After ten years of childless marriage to a wishy-washy, indecisive man she was enthralled by Roger's take charge attitude. He was so different from the loser who allowed himself to be buffeted by life's blows like an outclassed boxer. Roger was Elizabeth's divorce attorney, and from the very first meeting he had orchestrated her every move in getting her freedom under very generous terms.

Now she was single, and so was he. At first she did not let herself even fantasize about a possible romantic relationship. Roger was handsome and successful, and she knew that he had many female clients who were younger and prettier than she. In her early forties, Elizabeth was not expecting to have another man in her life any time soon, in spite of the fact that she was reasonably attractive with a trim figure. Not that she was opposed. On the contrary, her sexual fantasies had been raging for years. "Well, Elizabeth, it's all finished," Roger said during their wrap-up meeting. "You have enough money to live for a couple of years, which should give you time to get a job and secure your future. Our professional relationship is now over."

"I can't thank you enough, Roger. You have made a difficult situation almost easy."

He looked at her in a way she had never seen before. "You can thank me by letting me take you out to dinner. Come back to my office at seven o'clock tonight. Now, I'm afraid I have another appointment. My secretary will show you out."

Elizabeth was speechless. Not only had he asked her for a date, he had not given her a chance to answer. Before she could think of what to say, he was gone, and the secretary was there holding her coat. This guy has some nerve, she thought. He virtually ordered me to go out with him, like I owed him as payment for his services. What else is he going to order me to do?

That last thought sent a tingle down her spine. Being forced into becoming a submissive was one of her strongest fantasies, and Roger clearly had the strength of personality to dominate her. Had he seen something in her demeanor to encourage him in this direction? Was this what he wanted? Did she want it? Or did he not allow her to answer because he was afraid she would decline? No, that did not seem in keeping with his super-confident personality. Maybe he did have an urgent appointment and just didn't have time to extend their conversation.

All these questions raced through her mind as she got on the elevator.

**

Roger did not have another appointment. Deliberately he had decided to test his hunch that Elizabeth was a latent submissive. If she had reacted negatively to his arrogance he would have thought he was wrong. On the other hand, if she didn't respond, he would take that to mean that there was something appealing in his approach, in spite of her surprise.

He had used this ploy with women before. It was a kind of game to him, and it was a shortcut to finding the kind of woman he liked. Sometimes, if the woman was an overt submissive, she would respond immediately with 'yes sir', or 'yes master'. He did not like that. It meant she was too easy. Roger got his most satisfaction from bringing out the suppressed desires in women, breaking them in, as he called it. Afterward they were often disappointed when he made it clear he was not interested in an exclusive relationship, but usually they were grateful for the experience, and knew they would never again be content with vanilla sex. Many of them were still his friends, good friends, 'with benefits'.

Elizabeth intrigued him. She was an introvert, very prim and proper, but approached life with an intensity and curiosity that suggested there was immense passion just below the surface. He also liked her appearance, her dark hair and emerald green eyes, and her slender figure, especially her shapely ass, evident in spite of her ultra conservative clothing. If things worked out, that ass would feature prominently in their relationship.

No doubt an attractive woman like Elizabeth would quickly attract male attention now that she was single and open and receptive. But he had the advantage of having the first shot. He knew from his questions related to the divorce that she had never cheated on her husband; she was too shy and conservative for that. There was probably a lot of pent up frustration and lust buried in this newly liberated woman, and he was determined to go exploring.

**

Elizabeth fretted all the way home about what she should do. To just show up at seven o'clock at his office as ordered would be humiliating. The proper thing would be just to call his secretary and leave a message that he should call her when he had time to finish their conversation. But what if he never called? Their business with the divorce was finished, and she might never see him again.

There was no doubt that she was attracted to him. She liked tall men, and he was well over six feet. She liked men with dark hair and eyes, and he definitely had that 'Italian' look. She liked men who were intelligent and thoughtful, and in her experience working with him he had clearly demonstrated that quality. Then there was the way he had looked at her when he asked her to dinner. She had seen a smoldering sexuality and lust that made her feel like a desirable woman for the first time in a long while. By the time she let herself into her house she had decided.

Oh screw it. I'm going to do it. What do I have to lose? Now the question is what am I going to wear? Fortunately it's only eleven o'clock in the morning and I've got all day to get ready. I'd better be prepared for anything.

He didn't tell me where he was going to take me to dinner. Will it be somewhere casual or formal? Knowing Roger it will probably be somewhere quiet and elegant. I have time to get a manicure and pedicure and maybe even a bikini wax. I'm excited about what might happen tonight and nervous too. I haven't been with any other man but my ex. I don't want to disappoint Roger.

**

At 7:00 Elizabeth arrived at Roger's office building. She was apprehensive and excited, and still agonizing about her choice of clothing. Nervously she ran her hands down the simple black dress. Am I overdressed or underdressed? Having her hair and nails done had made her feel pretty, and to top it off she had splurged on a Brazilian wax, with a landing strip no less! She knew that whatever happened that night would be the beginning of a new her; there would be no looking back.

The building security guard opened the door. He gave her a big smile, as if he had been expecting a lady in fancy clothes to present herself.

"Hello, I'm Ms. Woods, to see Mr. Carlton," she said with more assurance than she felt.

The smile stayed on his face. "Good evening, Ms. Woods. You look very nice. Mr. Carlton is expecting you. Please come in. He's on the eleventh floor, and the elevators are just down the hall. If you wish you can leave your outside coat with me."

She returned his smile, handed him her coat, and headed to the elevator. There had been something in his manner that told her this wasn't the first time a woman arrived after work to see Roger. Oh well, she thought, What should I expect? He's an attractive single man.

The elevator jerked upward, and the upheaval in her stomach from the rapid motion merged with the butterflies from her nervousness to make her take deep breaths. Suddenly the doors opened and there standing right in front of her was Roger. She gasped as he reached out a strong hand and took hers. He smiled, but his voice was stern.

"You're late. You should have been here five minutes ago. Your punishment will have to wait until after dinner; we have reservations. You look very nice. Now get back in the elevator."

Once again Elizabeth was speechless. Punishment? What did that mean? Maybe she had misunderstood what he said. I'll just ignore it, she thought.

He kept holding her hand as the elevator started down. "I think you will like the restaurant. I picked for dinner," he said. "It's elegant, the food is good, and even though it's cold out, we can walk from here."

"I'm sure it will be fine," she managed.

His hand gripped her tighter, as if she might try to get away. "They also have private booths where we can talk. I want to know all about you."

"Oh," she said. "There's not much to know. I've led a pretty uneventful life."

"That's about to change," he said just as the elevator doors opened.

For the first time since seeing him she smiled. "Yes, I have that feeling," she said.

He led her down the hall and past the doorman, still keeping her hand in a tight grip. "Good evening Mr. Carlton," said the man with a slight bow. "You have a very lovely companion tonight."

Elizabeth blushed, and a warm feeling pervaded her chest. She began to relax. High adventure seemed to be just around the corner.

"Thank you George," said Roger. "She is indeed lovely. I am looking forward to getting to know her this evening. Please bring us our coats."

George retrieved the garments from a closet. "Here you are madam, just slip your arms in here. And now you sir. It's going to be bitterly cold tonight."

"Yes indeed," Roger agreed. "We are not going far. We'll be back later."

"Very good Sir. Stay warm." he said, closing the door behind them.

"George does an excellent job," Roger observed. "And he appreciates beauty when he sees it. You look absolutely stunning."

The words sounded sincere, and Elizabeth warmed again. She was liking Roger more every minute. "I appreciate your saying that," she said. "It has been a long time since I dressed to please a man." What did I just say? she thought. I hardly know this man, and I'm telling him I want to please him? How is he going to interrupt that? I've got to get myself under control.

"I am pleased, and I expect to be pleased even more as the evening progresses," he said. "Ah, here we are already. I told you it was close by."

The restaurant was small. A carved wooden door and one window faced the sidewalk. A tasteful sign announced the name, 'Roberto's'. The maître d in a tuxedo greeted them in the foyer. "Mr. Carlson. It is a pleasure. Your table is ready. What a lovely companion you have."

This could go to my head, thought Elizabeth. But I don't mind at all!

They were seated in a plush booth in the back corner of the darkened room. There were maybe a dozen other tables, most of them occupied by couples or groups of four. Thick carpet and tapestries on the wall muted the sounds. As soon as they had settled into the cushioned seats a waiter placed martinis on the linen-covered table in front of them. Elizabeth felt like a queen being entertained at court.

Roger raised his glass. "A toast to the beginning of our non-business relationship," he said. "May we both get the pleasure from it that we seek and deserve."

Oh my, she thought. But she lifted her glass and smiled. "I'll drink to that," she said.

"I have already ordered for both of us," Roger said. "A Caesar salad to start, followed by the wonderful white fish that is the specialty of the house. Their best Chardonnay will be served with the dinner. Now tell me all about you. Start with your first boyfriend, and don't leave anything out. I'll know if you do, and that will add to your punishment."

Punishment? There was that word again. No mistaking it this time, she thought. I can't let it pass. He will think I'm a nit wit. But why do I feel such a rush when he speaks to me that way?

"What do you mean 'punishment'?" she asked with a slight tremble in her voice.

He smiled. "Don't worry about that now. Sip your drink and tell me your story. What was your childhood like?"

She took a deep breath. "I was the only child of a couple of college professors. My mother taught English and my father History. Needless to say, education was the number one priority in our family."

"I'll bet you were a good student."

"Pretty good. I was shy and introverted, so boys and social life didn't interfere much with my studying."

"You didn't have a boyfriend?"

She shook her head. "Not until I was a senior in high school. My parents emphasized that there would be plenty of time for that after I got my education. They sent me to an all-girls camp every summer."

"You must have felt sexual desire during those years."

A warm blush crept over her face and made her hands sweat. She took a long drink and noticed to her surprise that the glass was empty.

"I see I touched a sensitive nerve," Roger said kindly. He reached out and put his hand on hers. "It's nothing to be ashamed about. If we are going to be the really good friends that I hope we are, you are going to have to go to those places and share them with me."

At that moment the waiter arrived with their salads. "Would you like the wine served now, Mr. Carlton?" he asked.

"Yes please. Then give us half an hour before bringing the dinner."

The pause in the conversation as the wine was served gave Elizabeth time to process what Roger had said. It was clear that a relationship with him was going to be unlike any that she had experienced. He was not wasting any time with pleasantries before bringing up the subject that was foremost in her mind. Never had she revealed her true sexual nature to anyone, including her husband. The thought was both frightening and exciting.

"What would you like to know?" she asked.

"Tell me what you fantasized about as you masturbated."

GULP...I sure hadn't expected that question! But I can't let him fluster me.

Smiling sweetly she batted the ball back into his court. "How did you know I masturbated?"

"Don't be ridiculous," he scolded. "Everyone does when they can't have the real thing. Were you imagining a handsome movie star making love to you?"

Elizabeth hesitated, and then decided to come out with the truth. She felt like she was under some kind of spell and it felt good. An inner voice was urging her to let go.

"I fantasized about being captured by pirates and being made to serve the leader as a sex slave." She sucked in a big breath. "There, are you satisfied?

Roger said nothing, but just stared at her with a slight smile on his face. His hunch had been correct. Ms. Prim And Proper Woods was a latent sexual submissive, who at this point in her life was ready to admit it and go with the flow. He felt himself harden in anticipation of what was to come.

"Well aren't you going to say anything?" she asked finally. "It was only a fantasy."

He loved her look of discomfort and vulnerability, and he deliberately prolonged the silence another few seconds before reaching for her other hand. "I am so happy you told me that," he said. "It confirms my impression of you. We are going to be very close, you and I. You see I am the pirate captain. My sexuality has always been linked to dominating women who are turned on by being bossed around in the bedroom."

Once again Elizabeth was at a loss for words. Roger had seized on her half-hearted admission and was taking her in a direction she was not sure she was ready for. "I said it was only a fantasy," she murmured.

"But one you turned to for excitement and pleasure, if only in your head. Don't fight it. You would be surprised at how many women feel the same way. Look at the popularity of 'bodice-ripper' novels, and the recent super-selling Fifty Shades of Grey."

Elizabeth could not deny the truth in what he said. She loved reading racy stories where the heroine was seemingly forced to submit and then had the best sex of her life. But reading about such things was quite different from doing them. She wondered how much experience Roger had in this area.

"So you've played this game with many women?"

He laughed. "Not that many. When I am sexually compatible with someone I like to have a long term relationship, just like my father. In fact I think I got my sexual proclivity from my father."

"Oh my. What do you mean that you got it from your father?"

"My father was a successful lawyer, just like me. He had a very commanding presence, and from puberty on I realized that my mother responded sexually to his strength. Then one night when they thought I was asleep I followed them to the basement and saw him half drag her by her hair into a room that was always kept locked. I hid and listened to the noises coming from that room. There were swishing and slapping sounds, and mother at first seemed to be in pain, but quickly her moans became sexual, and I knew she was a willing participant."

"That must have been quite a traumatic experience for a young boy."

"It was and it wasn't. I knew my parents loved and respected each other. Other kids parents got divorced, but not mine. And my own sexuality had developed in the same direction. I was masturbating to images of bondage and discipline. Eventually my father took me aside and told me that he and my mother had been in the 'lifestyle' for many years, and that it was nothing to be ashamed of if both people enjoyed and wanted it. My domineering, commanding father was devoted to my sexually submissive mother, and she adored him."

"I had no idea such things were possible in a marriage. My husband never took any initiatives in this direction, in spite of hints from me. And the only other man I have been with was a graduate student in college who gave me the 'slam-bam-thank-you- mam' treatment. He then had the nerve to tell me I was a cold fish because I didn't respond with much passion."

"What about sex with your husband?"

"It was okay at first, new and exciting. But then he seemed to lose interest. I think he was getting it on with the girls at the hospital where he worked. After a while I didn't want him."

Suddenly Elizabeth's eyes filled with tears. The realization of the futility of all those lost years trying to be the perfect wife came bubbling to the surface. "I'm sorry Roger," she sobbed. "I guess I still haven't gotten over the failure of my marriage."

"It's okay," he said. "Do you regret asking for the divorce?"

"No...no... I had to get out. I knew there had to be more to life than just taking care of a worthless, neglectful husband. My parents disapproved of my giving up, but they celebrated the fact that they had given me a good education so that I could take care of myself."

Conversation stopped as the waiter arrived with their dinners and refilled their wine glasses. Elizabeth was lightheaded and thought briefly about switching to water. As if he were a mind reader Roger raised his glass in a toast. "Here's to us," he said. "Don't worry about drinking too much. I'll make sure you get home safely."

"With my honor in tact?" she laughed.

"That's another issue," he responded with a grin. "You still are facing a punishment, and you may have to buy me off with your honor."

She blurted her response without thinking. "I'm aware of that," she said. "I think I'm ready."

My god, she thought, what did I say? I've just given him license to do whatever he wants to me! And the way he is looking at me now is scary! But I can feel the wetness between my legs.

Roger stared deeply into her eyes. He hadn't thought he could get any harder than he already was, but he had been wrong. Elizabeth held his gaze for a few seconds and then looked down. It was the classic signal of submission. She will need training, he thought, but she's already half way there. I wonder how far I can push her? This is going to be an exciting adventure for both of us.

"Eat your dinner now," he said.

"Yes sir," she replied, still looking down.

"I have a few more questions for you. You will answer me honestly and completely. Do you understand?"

She raised her fork to her mouth and nodded.

"In these fantasies of yours does the pirate captain tie you up?"