Jamaican Beauties Jaunt Ch. 01

Will's first message explained, "The following is a summary, or synopsis of my love and sex life. It focuses on how those relationships shaped my attitudes and philosophy. It's a sad story I've entitled "Unlovable Will's Story." If, at any time, you require additional information, please send me a message and I will pause and try to answer any questions you have."

"This is going to be interesting," Denise thought as she settled into her easy chair and prepared to read the story of Will's love life.

Will's next message read, "Although I've had a successful career and I'm financially secure, I was never successful in finding someone that loved me enough to want to marry me and spend their life with me. I met my first love the summer before we entered high school—what you call secondary school—she was my best friend and the girl to whom I gave my virginity and who simultaneously gave me hers. She subsequently told me that we could be friends, even occasional lovers, but she could never marry me. Her focus was solely on going to college and having a career. Furthermore, she was devoutly Jewish and would not consider having a gentile husband."

A quarter minute later, he sent the next message, "My other high school love told me she would always love me and would willingly be my sexual partner whenever I needed one. However, her focus was on college and her career, as well as many other things she wanted to do in her life. She insisted she was not ready and did not want to be in a dedicated relationship, especially a marriage. She first wanted to enjoy as many sexual partners and encounters as she could before she settled down with just one man or woman."

Since Denise had not sent a message, Will continued, "I had two other brief encounters in high school, both practically one-day stands in terms of sexual activity, but neither included sexual intercourse. They ended when each girl told me she believed the two of us did not have a future as a couple, the first because she was Catholic and I wasn't, the second because she lived in Dallas and I didn't."

"How sad for you, what did you do?" Denise sympathized and typed.

Will, hoping it would answer her question, sent his next prepared message, "When I graduated from high school, I was fortunate enough to be accepted into the University of Texas where I focused on studying so that I might graduate with honors. I did well enough to receive a partial scholarship to graduate school at the University of Pennsylvania's Wharton School of Business."

Will's next message explained, "I should point out that I wasn't without companionship during college. In each school, I continued my friendship and sexual relationship with each of my two high school lovers—the two women with who I'd had sexual intercourse. Those relationships included living and sharing a bed with each woman—one at Texas and the other at Wharton. However, neither advanced from a temporary arrangement to a permanent relationship. Both ladies remained steadfast in their objections to marriage with anyone including me, I should say, especially to me."

"I'm confused as to how you maintained a relationship with two women whom you say had no desire to have long term relationships with you," Denise wondered and then typed.

"We were, and still are, best friends. We continue to get together and we occasionally have sex with one another. However, neither woman, each for her own reasons, wishes to have an exclusive relationship with me or any other man. In fact, neither has ever married," Will replied.

"It all seems so strange, but please continue with your synopsis of your life and loves," Denise commented and requested.

Will immediately sent his next prepared message, "After graduate school I went to work in the Dallas office of an agency of the U.S. Congress. There, I met and soon fell in love with a co-worker. We were compatible in many ways. For instance, she was, like me, willing to do whatever was necessary to accomplish the job. I often wondered if our focus on our jobs would affect our relationship. Yet, our relationship flourished and I eventually introduced her to my mother and stepfather. Later, I proposed to her and was ecstatic when she accepted. At last, I'd found a woman with whom I wanted to spend the rest of my life and she said she wanted the same thing."

Denise thought to make a comment, but decided to let Will continue without interruption.

Will's next prepared message read, "Suddenly and surprisingly, my joy and our relationship ended. A company offered her a position she had long worked toward and hoped to obtain and she immediately accepted. Unfortunately, the company and the job was in California and required her to travel extensively and work long hours, including weekends. She soon left for her career opportunity of a lifetime, temporarily at first. Then, because it was always difficult for either of us to get away from our jobs, our temporary arrangement morphed into a permanent separation. Five months after she moved to California, she called off our engagement, explaining she was too busy to maintain a relationship and she believed that continuing our nonexistent relationship was unfair to me. She at least conceded she wanted us to remain friends and perhaps occasional lovers."

"Oh Will, three lovers, three broken hearts. I'm finding it difficult to get over one. How did you survive, how did you get through it?"

Will typed, "I've found that, like so many things in life, you just have to keep moving forward until you get through it. It can often be difficult at first, but in time, it doesn't feel as bad as you first thought it would. Then, one day, you realize that getting over your loss wasn't as hard as you initially believed it would be. I believe it's one of the many ways that God and the angels help us get through our difficulties, to move on, to again enjoy life."

"I hope you're right, because I'm still feeling miserable. But I digress, please continue your story," Denise confessed and requested.

Will immediately sent his next prepared message, "I was twenty-seven, and I was living a very good life. I had several good friends—primarily ex-girlfriends. I had a good education—a bachelor's degree in computer science from Texas and an M.B.A. from Wharton. I had a successful career as a computer auditor with an office of the U.S. Congress. I had a mother and stepfather that I loved and I knew loved me. I dated numerous beautiful, intelligent, and extremely sexual women, but always on a temporary or occasional basis. Overall, I had a good life and a good future. Nevertheless, I didn't have what my stepfather had, the one thing I'd always wanted and wished for: a woman who loved me and wanted to live with me for the rest of her life."

"I think that's really what we all wish for—someone we care for and who cares for us," Denise acknowledged.

Will did not respond other than to send his next several prepared messages, "After contemplating my life to that point, I concluded I wasn't meant to be happily married. History had proven I obviously wasn't the guy women wanted to marry. However, I had neither the desire nor the tools necessary to become a stud, a guy women lusted after. I decided I would strive to become the nice, polite, reasonable guy that was everyone's good friend."

"It seemed to me, based on my previous experiences, I was intended, perhaps it was even my reason for being, to help women find themselves, to show them how to enjoy their lives, and then to help them move on with their new lives. To that end, I strove to be the kind of person girls wanted to talk with when their arrogant, unconcerned, or uncaring boyfriends abused, ignored, or dumped them. I soon became the guy that looked at women's problems with an analytical, unemotional, and logical mind and offered them reasonable, useful, and workable solutions."

"Soon, I was a friend to all the ladies I knew, but never their boyfriend. I was their occasional companion, never their steady date. I was the guy women asked to go with them to office functions, weddings, or formal parties. Occasionally, they asked me to spend the night with them, but they never asked me to meet their parents. I thought of myself as the guy in a song from one of my stepfather's Rock and Roll oldies CDs. The first time I heard them, the lyrics struck a nerve, "If your broken heart should need repair, then I'm the man to see."

Without a message from Denise, Will sent his next prepared message, "That became my focus, to be that catalyst, that person who assisted women to overcome a loss and become who or what they wanted or desired. The guy that aided and abetted them in achieving their life goals. I was the guy in the song, the guy everyone called "Handy Man." Fortunately, helping those women also meant I frequently had marvelous dates and wonderful sex with many beautiful and intelligent women. "

Denise wondered if he was playing "Handy Man" in their relationship, but decided against asking him.

Will's next prepared message arrived, "A year after coming to that conclusion, I left my job with the U.S. Congress and, along with several friends, started what soon became a successful and financially viable company. I rarely dated during the first several years I was working to build the company. After it became viable, robust, and profitable, I met an interesting woman who ran her own company and had no time or desire to have a permanent or long-term relationship. We liked one another, found we were intellectually and sexually compatible, and we agreed to date. She, like me, had suffered numerous failed relationships. We dated for over two years. However, she decided that we'd healed one another and it was time for us both to move forward."

Will didn't wait for Denise to comment before sending his next message, "I was alone again. I went back to being the "Handy Man" and had to be satisfied with numerous brief, but unsatisfying, encounters. Fortunately, my business allowed me to travel extensively, and I continued to meet and date numerous successful, intelligent, good-looking women. I dated some of those ladies irregularly for years, others exclusively for a short period, many for just a weekend. However, as with the women I'd dated in the past, those relationships were never serious; those women were not looking for nor expected a long-term, exclusive relationship. For several years, my life consisted of long days of work interspersed with short-lived sexual relationships that were never destined to become permanent."

"And that is where you are now?" Denise messaged.

"Actually, no," Will typed back, "A few years ago things changed. The company was a success and I was free to do whatever I wanted. That's when I was afflicted with what many call "the middle-aged crazies," which in turn led me into a series of life-changing relationships. I tried a gay relationship, which lasted half a year before it too ended, just as my earlier heterosexual relationships, when the guy left for a new career in California."

Denise literally gasped and said aloud, "He had a homosexual relationship? My goodness!"

Will, even though he did not know her reaction, intuitively knew to skip the next message, which described his homosexual relationship, and instead sent the succeeding prepared message, "While I was grieving the loss of my gay partner, I was surfing the internet, looking for a distraction and I met two black sisters in a chat room. We chatted for many months, became friends, and I made several trips to visit them. The three of us enjoyed each other's company, went clubbing together, dated, and had numerous escapades. As I noted earlier, the company I'd formed with my friends was successful and I was financially secure. So, I took a sabbatical, bought a house in Fort Lauderdale, Florida, moved there with the two sisters, and the three of us lived together in a ménage à trois—which is, interestingly, French for household of three."

Still not seeing a comment from Denise, Will continued, "A year later, I concluded the ladies were ready to start their own careers, to lead their own lives, lives that did not need nor should involve me. For a change, this time I was the one that moved away. However, I didn't simply dump them! Although, I moved out, I contracted them to remain in the house as live-in caretakers and agreed to pay them a salary that covered their living expenses so that they would be free to start their new careers and lives."

"Will, you have certainly led an interesting life," Denise quickly typed.

"There's more," Will typed and sent before sending his prepared text, "When I left the sisters, I was forty-one years old and very well-off financially. I moved back to Texas and into semi-retirement at my lakefront house, in a gated, adults-only community. Technically, I remained on sabbatical although I occasionally worked under contract for my company. That's when an old friend contacted me. I'd met her when she was an account manager at a company where I, while employed by my company, was in charge of contract work to assess their computer security. She informed me that she had recently divorced, was now the director of her agency's office in Dallas, and she'd specifically requested that my company assign me to a new contract to develop a training course on computer system reliability and security assessment."

The next message followed immediately, "It turned out to be a wonderful experience; we worked together well, quickly developed the course, renewed our friendship, were assigned to teach it throughout her company, and subsequently became lovers. Last May, as we enjoyed a romantic week at a Jamaican North Shore resort I asked her if she would consider a long-term relationship and commitment. Unfortunately, she informed me that she had recently come to the conclusion that the two of us could never be happily married, a couple, or anything other than friends, albeit with sexual benefits. After we discussed the reasoning behind her conclusion, we mutually agreed to end our exclusive relationship. It was after that vacation, in an effort to forget that I was again alone, that I decided to check in on some of my favorite chat rooms. That's when I met you."

Seeing Will had finished with his story, Denise offered, "Wow! Again, you've had a much more interesting life than the one I've led. I must say, I'm amazed at how positive you've remained despite all the heartache you've suffered."

A half minute later she received Will's response, "Denise, as I've told you before, if you don't focus on the bad stuff it fades away. Furthermore, if you stay focused on the good things, the happy moments in your life, you'll always have pleasurable memories."

Denise messaged "Thank you Will and good night," before she signed out of their chat. After she'd refilled her wine glass and reclined in her easy chair, she smiled to herself as she thought, "Will, like father, is always trying to cheer me up. He's always reminding me to focus on the positive things in my life."

* * * * *

Undesirable Denise's Story

The next evening, it was Denise's agreed upon turn to share the story of her life and loves with Will. When she had insisted that he share his with her, at his insistence, she had reluctantly agreed to do the same in return. Seeing how well it had worked when Will told his story, Denise had spent much of her afternoon preparing her own story. She, as Will had, used short paragraphs, which allowed her to quickly paste and send messages while giving her the time she might need to read and respond to his queries.

Will was surprised when she began their scheduled chat session by immediately sending the message, "My life story, which I've entitled "Undesirable Denise's Story," is rather boring. I haven't had much of a life and even less of a love life, especially in comparison to yours. That aside, I would like to start out by telling you what led me to the chat room where we first met, which is also what lead me to want to know more about your life and loves."

"Denise, it's your story. Please feel free to tell it any way and in any order you wish," Will obliged.

Denise sent her next prepared message, "A little more than six weeks ago my Belgium boyfriend and I separated, or more correctly, he broke up with me. After I'd spent a week showing him my favourite spots in Jamaica, sharing a hotel room and a bed with him, and offering myself to him without condition, he flew back to Brussels and immediately sent me an email telling me he no longer wanted to have anything to do with me. Then, the day before you and I met online, I learnt that during our Jamaican tour, my so-called boyfriend attempted to engage in, and may have had sexual liaisons with several girls he met during our tour of Jamaica. That knowledge, whilst hurtful, at least explained his various excuses, frequent unwillingness, and inevitable inability to engage in consensual intercourse with me on the few nights we attempted to do more than sleep in the same bed. Although it was a hurtful experience, it was just one more episode in my life proving I'm not attractive, sexy, or worthy of being loved."

Will tried to console her, "Denise, first, I have seen your profile photos and you are clearly a beautiful woman. Second, from chatting with you, I'm confident that most men would find you to be an extremely sexy woman. Third, we are all worthy and deserve to be loved. Finally, if you ever want to talk, I think I could help you figure out what you should do."

Denise immediately responded, "How would you know what I should do? Have you ever been duped and dumped by a cheater?"

"No, but I'm older, I've had more experience in relationships and especially with breaking up."

"Really? How many women have cheated on you and then left you?" Denise asked.

"None that I'm aware of. However, I've had my heart broken at least four times. Each time by a woman I loved, a woman I was willing to marry. Uncountable times, I've broken up with women that I cared for greatly. Thus, you see, I've had a good deal of experience having someone I love break up with me. I can sympathize and perhaps even empathize with you. I think I have an idea of how you feel and, more importantly, I know what to do to get over the hurt. I know how to help you move on with your life."

Ignoring his message, Denise typed, "With my loves out of the way, let me tell you about my life. Some of it you already know, but I thought it might help if I put it all in context. This is going to be difficult, so, unless you become lost or confused, please don't interrupt."

"Sorry, and I won't," Will obliged.

Denise's next message read, "As a child, I never measured up to my older, pretty, and athletic sisters. I watched as my father doted on them. He coached them in several sports, attended all their games, and constantly talked about their athletic talents. After my sisters went to boarding school, I hoped it would soon be my turn to garner my father's attention. I must admit, he tried to give me that attention. Starting when I was six, my father had me try out for every sport he knew, but I was never successful at any of them. Father coached me, assisted me, and even dared me, but to no avail. Unlike my sisters, I was not thin, agile, and athletic; instead, I was large, ungainly, and inept. No matter how much father coached and coaxed me, I never excelled physically or even demonstrated minimal abilities in any athletic activity."

"Playing a sport isn't all there is to life, and it should never be the definition of someone's life," Will argued.

Ignoring his comment and interruption, Denise sent her next message, "When I was eleven and about to enter Secondary School, father, after five years of trying, gave up coaching me in sporting activities and, as an alternative, introduced me to the arts. That was the best of times in my life, times I still look back on with a smile on my face, happiness in my heart, and wonderful memories in my mind. We spent hours together every week, going to concerts (from classical to hip-hop,) dance performances (from ballet, to stage productions, to modern, and even to calypso dances in the local clubs and during the Bacchanal festivities,) visiting art galleries (from the classics, to modernist, to contemporary Jamaican, and even the new street art,) and going to every museum in the Kingston area. Most weeknights, during dinner and afterwards, we talked endlessly about whatever novel, play, or poetry I was reading. I didn't think life could get any better, until father took me to dance class."