Second Act Pt. 01

Interlude

Brett always preferred older and mature women in his younger days. He had enjoyed a marriage with one for ten great years and had a wonderful son together with her. He always felt it signaled confidence and maturity, being with a woman two years older than himself. He had loved his life with her and was heartbroken when she suddenly passed, the result of some quick and unforeseen health problems.

For the past two years after her death, he barely even thought about women. His days were filled with a challenging yet enjoyable job, some minor business travel, and enjoying every moment with his son. Though he felt lonely at times, he had a good network of friends, supportive parents nearby to help with his son, and an overall deep personal support network.

Now 37 and settled in a good routine, Brett finally was starting to think more about what he wanted out of the next ten years for himself. It was the type of thinking that had not even been on his radar in the first few years since the loss of his wife. He had been in survival mode early and then solely focused on his son's needs. But now, it was like springtime in his mind as he thought about what he wanted. What a strange thought, he often considered, a weird concept, so foreign had it been to his thinking.

One such area of thought was about his sexual life. Brett was an attractive young professional, with coarse brown hair, dark blue eyes, athletic build, average height and weight, and an overall very handsome and well-do keep. He knew he was a hot commodity and had received many flirtations and advances from women all over the place since he became a bachelor again - 100 times more than when he was a married man. He was certainly not used to some of the aggressive flirting and had become much more adept at picking up on it over the last two years. The attention was flattering but was usually from women his age who were widowed or divorced.

Though he was attracted to some of these suitors, it was problematic that they wanted commitment and a relationship, a man who had a good job, good money, and a great son. He was a wonderful father in their eyes - great husband material! That is the last thing that Brett wanted to feel or have expectations of from another woman in his life. He did not want to replace his wife, did not want to be committed to anyone other than his son or family for the foreseeable future, and did not need extra-added responsibility.

He also wanted more primal, rougher, and better sex. He desired someone focused on his pleasure and his desires. He often thought back to how sex was with his wife. It was regular although not enough for him. More than that, it lacked spontaneity, variety, fun, intrigue, adventure. It was the same, over and over again. Both he and his wife were not very sexual with each other from the beginning. When he tried, over the years, to initiate more, spice it up more, it was met with all of the darts and arrows of health issues, work and career dramas, and most importantly, body image issues. She simply could not get over not being twenty forever in terms of her body and her weight/shape was always a sexual firewall, regardless of approach by him.

He also had changed a lot over the years sexually. He had just started becoming more comfortable telling her what to do, what he liked, what he wanted out of their sexual life together. It had, after a year or two, started to finally soften her and result in some fruit, but then the doctor visit. And that was that.

For years, he realized that his relationship with his wife was one of companionship and partnership first, sex somewhere down the line, even though they were both very attractive people. He waited on her to initiate and put her needs first. He was never forceful with her or commanding with her during sex, even though he wanted to be. He realized that this was a mistake well into his marriage, as he basically had to let these desires go because he had subverted them for so long. It was hard sledding, making some of the changes he did make: initiating more, being more sexual with her. He often thought that all would be easier if he could just start over sexually with her - or anyone. How you start is incredibly important to how you continue, he realized.

But now...there was an opportunity to sexually start over with someone else, and not in the context of a long-term-relationship. This thought began to intrigue him and started to occupy his mind more and more on a daily basis. What would a relationship like this look like in his current context? Who would be the ideal person? What did he really want out of sex with another woman, at this point in his life?

He started making a list of the ideal person that he could set the right scene with, who would allow him to try many of the things he wanted to try. The first requirement: young and unattached. The second: uncertain and still learning, almost unsure of themselves. He wanted someone who he could mold and shape sexually, who had an adventurous yet very submissive longing, a desire to learn things about their sexuality with him leading.

Finally, unattached was also very important. But again, young and unattached. He did not want someone thinking that he wanted anything other than a fun experience of learning and mutual discovery. She needed to know and expect that this was about doing something for each other sexually that had little to do with everything else in life. Perhaps a girl in college or right out of school who was on her own and doing well, not looking to get married or get into a relationship just yet but who is horny and desiring to submit to an older man who is well-established and comes with less drama?

On his next business trip, after a hard day at work, he was reading an online news story about a female college athlete who had been having an affair with a 40-year old professor. He was always intrigued at these types of stories, as he had ready many over the years. He decided to look up to see if anyone had written more on the story and, sure enough, he found a local student-run college blog from the university community of the student in the story. The rumors were that the student had been serving as a sexual subject to the professor, a married man with three kids. This made Brett very excited. A young woman at her prime serving a man about his age in a sexual capacity - that's what he wanted. Now, he just had to find the right subject.

The Second Act

Over the coming weeks, Brett decided to do his research and came up with the idea of creating some profiles on a few BDSM dating service sites. He shared about his situation and what he was looking for and signed up for a couple. He also browsed through profiles of willing 20-25 year old submissives in the area. He was thankful that there were several large colleges in his metro area and there certainly were a lot of young ladies in this age range whose interests and kinks were eye-popping. Then there others who simply stated they were submissive looking for an older dom without a picture.

He realized after a few weeks of being on the site and only having a few dead-ends, that he would need to actually initiate some conversations with some of these girls. As after he had learned with his wife years ago, the man needs to be the initiator. These young ladies were waiting for a leader, someone to take them by the hand and lead them to understand their sexual desires as a responder and object of desire - his desire. So, he gradually started to reach out to any of the local profiles who piqued his interest. He sent some very thoughtful yet concise messages over the course of about a week.

It was early August, and Fall was still a good month out. His son would be heading back to school soon. Even though he was in camps and what not, Brett was still looking forward to a more normal school-year routine with his son. Routine was important in his life, but he sensed that part of what he was looking for was someone to help break his routine, someone to focus on going somewhere exciting with him in an unexpected manner.

He received a few interesting inquiries and chatted with a few subjects back-and-forth, for a week or so. But none of these really panned out.. Then, he noticed in his chat inbox, a reply message titled "Hi...chat sometime?" He liked it. It was fun, shy, youthful, and simple. This is what he wanted. Not some polished and put-together professional but a shy, young, eager type. He remembered writing this particular profile. She was 21 years old, a local university junior whose profile showed that she was 5'5, 120 pounds of lean beauty with dark, frizzy hair, down past her shoulders in her bio pic. She had cute dimples, a great smile,, and her eyes were a perfect shade of blue. He really liked the looks of this one. His arousal became apparent to him as he sat and pondered an actual meetup with this girl. His breath and excitement began to escalate.

The small coffee shop was somewhere he felt very comfortable. He had not been there in about fifteen years, since he got engaged. However, prior to that, when he had lots of time on his hands, he would come to read, study, and pass away some free time. It was a walk down the street to his old house that he used to rent when he was a young professional out of grad school. The university where he completed his graduate studies, the same university where his prospective subject was studying as an undergrad, was about one mile away, so it used to be very convenient to his pre-marriage, pre-family, bachelor life.

He wondered if his candidate, who was supposed to meet him at the shop in a few minutes, was walking from her college apartment. Did she live with other girls? In a house, dorm, etc. It all seemed like so long ago, that phase of life. Would she be creeped out by his age? If so, surely she wouldn't be meeting with him. No, she would be the one who was the most nervous, after all, how much humility would it take to admit that you wanted to be under the control of a complete stranger, that you desired to be sexually used by another? That is what he had wanted in his profile and that is what she seemed to state in hers, in not-so-much-language. He was half beginning to wonder if maybe that would be too much for anyone when...

They had agreed to meet over lunchtime for a chat. She was between classes and he wanted to see her during a normal daily routine. Besides, it was easier for him to meet during the day. He was dressed in dress pants, a button down, a blazer, and preppy tie. It was a hot summer day, so he didn't want to go all suit-and-tie, but he also needed to show authority and professionalism, as he knew this was important in establishing dominance. She strolled in nervously but trying to act confident, he could tell. She was striking from his perch in the corner.

They had only seen each other's faces before, but the rest of her was even better than her very cute face. She wore her curly hair down, just as in the picture. He could tell that she had worked hard on this hair today, maybe even skipped class to get it just right, by the looks of it. That one factor told him that she was very nervous about this meeting - she wanted to impress. She wore a summer dress, which pleased him very much. He hadn't told her what to wear, and she had selected such an appropriate and well-thought-out dress. It was off-white, thin material that hugged her nicely, showing her excellent shape, yet it was very classy as well, showcasing that she was not a slut by nature. To top it off, she wore platform shoes that raised her ass a little and put it on proud display.

Her posture seemed to be very good for a girl of her age. He was impressed by that. He certainly loved what he was seeing - a sharp jawline and plunging neck down to a very nice set of breasts, her nipples slightly poking out from behind her dress even through her bra. She had runners' calves and definitely a nice, firm runner's ass. It took her a minute to turn around and he waited until her eyes met his. He smiled softly while gazing into her eyes, purposefully getting lost in that deep blue. Then, he did a half-wave and began to rise from his cushy chair, one of two in a private corner of the shop. He confidently strolled over and introduced himself to her.

"You must be Katie, even more stunning in person," he stated as she kind of elegantly stumbled forward in the middle of the shop to meet his confident stroll up to her. He extended his hand to meet hers, shaking firmly but with much control. He nailed the compliment, he could tell by her cheeks blushing.

"Yes, I am," she awkwardly stated. She didn't know what to say, it seemed, and was nervous to say the right thing.

He looked to ease the tension with normal talk. "I've got us a comfortable spot over in the corner. I'll order something for us if you want to get comfortable right over there."

"Oh, okay," she stammered as she found her away to the comfy two seats he gestured towards.

He wondered if she was confused that he was going to order for her, not even asking what she wanted. This was not like him, but he wanted to take control of the situation from the very first interaction and not ask her what she wanted but instead show leadership and confidence by ordering for her. Besides, it was summer and she had to go back to class, so he ordered her a veggie-infused sparkling non-alcoholic frizzy drink and himself a sidecar.

They talked for at least forty five minutes about everything under the sun. He wanted to relax and desired for her to relax as well. The topic they were there to discuss, or potential arrangement, was stressful enough. Still, he had to remain mysterious and somewhat aloof as he knew that was an important part in this younger woman/older man dynamic. He had read that much in all of his research.

He learned that Katie was about three hours away from home, a smaller regional city in a more rural part of the state. She grew up in a fairly normal family and loved the structured life she left behind. He sensed from asking about her family that there may have been some issues with her dad not being assertive enough with her, but who was he to know? She was the oldest of three , the crown jewel of her family, the first off to college among the kids, on a scholarship, multiple good career options in front of her leading into her junior year. But now the pressure was starting to mount and Brett could tell that she needed some discipline, structure, and control amidst the chaos of all of the decision-making she was constantly juggling. He asked a few questions, halfheartedly, about guys she had dated, which caused her to blush.

He knew he needed to not beat around the bush but get things to a sexual place fast in order to set direction for this relationship. After asking her if she had a boyfriend (which her first boyfriend had been her senior year of high school and then a few college ones for a few months each - 4 in all), he asked Katie very matter-of-factly, "how often did your favorite boyfriend fuck you?" It literally stunned her. The conversation had been so polite and well-mannered, so professional. She was blushing. With her eyes down, she tried to platonize the act.

"Last year, the one I liked the most, we had sex maybe once a week after we dated for a few months and it lasted a few months after that." She was shaking.

"Thanks for answering, Katie, I know that was hard...it will only get easier if we continue. And I appreciate your honesty. But you didn't honestly answer my question. I asked you how often your favorite boyfriend fucked you not how often did you have sex? Either I am to assume, by your answer, that you've never been properly fucked for having sex and getting fucked aren't the same thing, or you have been fucked and you're just too shy to say in your answer to me, out loud, I was fucked x number of times by my favorite boyfriend. Which is it, Katie?" She was somewhat petrified now, licking her lips, thinking of what to say, but he could also see, as he gave her body a glance-over, that her nipples were hard-as-a-rock.

She admitted next that she had never really been fucked by any of her boyfriends. They were all silly, shy, or had no clue what they were doing. They were constantly nervous, not sure what to do, and sex was very uninspiring with the few who she had been with. She had a limited sexual path, only having sex with four guys and only a dozen times or so total. She had performed oral sex on two of them but it was very awkward. They were all weak and passive, by Brett's estimation, like he used to be. He could himself in these young bucks.

Katie wanted and needed more. She needed a true confident man. He could ascertain that she had trouble even saying the word fucked. So, how could such a shy girl be on kink dating site with so little experience, yet interested in some of the things she was interested in? He found out in continued conversation.

She shared that she had a roommate freshman year who told her all about her experiences with an older man and all of the things that they had done. It was her roommate from sophomore year on a snowy night with a bottle of wine, crackers, and cheese spread out before the two of them, sharing with her the details of a man she had met Freshman Year who had done things to her that she never would have dreamed that she would have liked or let anyone ever to do her but also things that, now that she had experienced them, could not go one night without fantasizing about and getting herself off just thinking about experiencing them again. She shared with Katie what it was like to be taken, all of her body, mind, and soul, by a real, dominant masculine man, an older man who knew what he was doing and knew how to bring something wild and raw out of a young lady.

The conversation flowed much better after Katie started talking more and after he began to encourage her to use certain risque words that he could tell she wasn't used to using - hell, not even he was used to using them but she didn't need to think or know that. For instance, he would only interrupt her discussion of learning about things from her roommate and ask her to be more specific. When she talked about her roommate telling of this man making her roommate please herself in front of him, he would say, "were those the words she used, Katie, in the story?"

Katie would say, "No."

Then, he would say, "If we were to get together, sweet Katie, I would order you by saying: Take off your bra and panties, Sweet Katie, and spread your legs, with one hand, play with your nipples and then I want you to finger your pussy...I want to hear you make yourself moan, my sweet slut."

He must have interrupted a dozen times to either have her clarify the recollections of her first learnings from her roommate by making her says words like cunt, pussy, ass, tits, fuck, and cum instead of words like vagina, butt, breasts, have sex, and masturbate and orgasm. She was hot and bothered. As things went on, she was getting sexy comfortable with him, for she had now leaned into him and, after he had started by touching her, she had now gotten used to putting her hand on his arm and having her knee and ankles brushing against his. It was at this point that Brett took his cue.

"Katie, in just the few hours that we have sat and talked, I see that you are a delightful young lady with a bright, attractive future. I would love to help you and would consider it a huge advantage to have you as a part of my life...of course, you know what I am seeking out of a relationship. You are indeed a sight to behold and I would be delighted to have you serve me and get the things you are hoping to get from me. What are your thoughts""

Brett already knew that she would be putty in his hands after this. She was literally dripping wet through her dress and her nipples were rock hard through her top, her breathing excited and her face very glowy. She was fidgety and practicing all kinds of nervous ticks. She put together a few coherent sentences and some qualifiers and tried to ask some follow-up questions.