As a reminder to you, my name is Jack. A few years back, I made a bundle from stock options I was granted for working for next to nothing for a start-up internet company. I got myself into shape and bought a house on a golf course. As a bonus, I sort of weaseled my way into a group of middle-aged women, better known around the club as the Fearsome Foursome, due to their abhorrent, and often dangerous, golfing skills. The ladies were very attractive and I was fortunate enough to have been seduced by three of them, Irene, Anna, and Rebecca, who had just recently moved away. The fourth was Sheryl.
About six months had passed since Rebecca moved away. The sex with Irene and Anna was still incredible, when it occurred. There were some weeks that they couldn't meet, and there were others where we had it almost daily. Irene started to talk about counseling with her husband and Anna had mentioned that she met a nice guy who had taken her out on a few dates. I knew that, if these things worked out for them, we would not be sleeping together much longer. So I relished each time they came over.
Sheryl's daughter, Jessica, was graduating from college, and Sheryl and David were throwing her a party. I knew Jessica fairly well from being over at Sheryl's for various "foursome" functions. We liked to kid each other about our alma maters, since they were bitter rivals. I would tease her that when she finished with her "prep school", was she going to try to get a real education or go through life ignorant. Her reply was that, since my school was out in the country, she "had too many teeth to go there."
Her taste in boys irritated her parents to no end. I had to agree with them too. These guys looked like they never had seen a barber; much less a razor, and their clothes were three sizes too big. Style was an ever-changing beast, I guess.
But Jessica was incredibly intelligent. She was graduating with double majors in Education and Economics. Her ambition was to be a college professor, so she had her Masters and Doctorate ahead of her. I wish I had one-tenth of her brainpower.
Jessica also wasn't one to talk about herself; so most of what I knew about her personally, came from her parents. In high school, she was a star basketball player, but her height, or lack of it, prevented her from playing in college. Being a competitive athlete, she took up track and became an NCAA All-American. Being an athlete, the only things I ever saw her wearing were sweats, baggy t-shirts and minimal, if any, make-up. Not exactly the most feminine of looks.
For her graduation present, I needed something that would befit her mind and also be somewhat practical. I found an old text about the trade practices of the ancient Greeks and Romans, so that she could start her own personal library. For the practical side, I inserted four tickets to an upcoming concert inside the book and a couple bottles of some flavored rums on the side, so she could party with her friends later.
I am the type of person that if an invitation says 7 pm, I get there at 7 pm. If they wanted me there later, why didn't they put the time later? Must be a guy thing! And not having a woman to wait for, I was always on time. I was the first person to arrive and was met at the door by David, her husband. He escorted me into the den and offered me a drink.
David is a brilliant real estate developer and has strong political ties with the local and state authorities. He had been tutoring me, so to speak, on the intricacies of the real estate business and gave me pointers on handling some of my real estate investments. David would not be considered a "hunk" by women's standard. Standing at 5'7", he may top the scales at 135 soaking wet, has a beanpole frame, balding and glasses. However, David has an incredible sense of humor, a quick wit and a love of sports. He told me, while in college, he ran the statistics for the athletic department. Watching any game, he could spout off the stats on a player, team and coach. I liked David, as did most men, despite his appearance. Women did too; I guess they figured him to be harmless.
Guests began to arrive and I mingled around, meeting as many of David's associates and cronies as possible. It never hurts to get plugged into the system. I turned on the charm as best I could so that I would be remembered at a later date.
Sheryl came down looking spectacular, of course. Her dress was knee length, but what caught the men's eye was the fact that it revealed a lot of cleavage. The bra she wore must have been industrial strength to hold those puppies up like that. She made her way around the room saying her "hellos", and when she came to me, I was one of the fortunate few who received a hug.
I whispered in her ear "You look radiant tonight." She gave my hug a little squeeze, thanking me for my compliment. Having those beauties pressed into me was a real turn-on.
Sheryl got everyone's attention and then introduced Jessica, as she made her entrance. I really didn't have much interest in her arrival, since I already knew her, so I headed to the bar for a refill. While standing there, waiting for the person ahead of me to finish pouring his drink, I felt a hand on my back and "Hey stranger, make one for me too?"
I turned and nearly lost my breath. The woman in front of me was not the Jessica I knew. This one had her hair done; her make-up applied and was donning a beautiful tea length black dress. Taking a second to recover from the shock and another to take in this amazing sight, I spouted, "Who are you and what have you done with Jessica?"
She laughed and said, "I know, not my normal attire is it? Mom made me. I wanted to wear something entirely different."
I took her hands into mine, and taking a feigned legitimate look at her body, "Take my word for it Jessica, this look definitely works for you. You look gorgeous." Seeing a little blush, I added, "So what will you be having?"
"Whatever you're drinking will be fine."
I poured our drinks and she escorted me out to the patio. Walking behind her, I got a great look at her ass and its swing. That athletic body poured into that dress made my loins ache with desire. Once outside, she found a place where we could talk. I took every opportunity to admire her too. Her breasts would never rival her mothers, but they were nice just the same.
I asked her, "So where's your boyfriend? I got the impression that you two were engaged to be engaged, or something like that." She gave me a sneer and said, "That asshole was a leach. He would have preferred to live off of my daddy's money or me than get anything for himself. Mom was right about him. She said I need to take a break from looking for men, and then the right one will come along." She paused a second and said, "So why aren't you married with a litter of kids?"
"Me?" I snickered. "I really haven't found the one for me yet. Maybe I am just too picky. It's tough finding someone that is interested in me rather than my money."
We talked for a while, and I found myself more and more captivated by her. She was not only beautiful, but also smart. There were relatively few subjects that she couldn't converse on, and when she couldn't, she listened. Just as it started to get interesting, her mother came over and told her to mingle with the guests. I stood as she walked away, watching her move through the crowd. I saw that Sheryl was giving me the eye, so I told her "That girl is going to be breaking some men's hearts." She nodded, still watching me watch her.
As the party ended, as usual, the foursome was the last ones there. I cornered Jessica and feeling like a schoolboy, asked her out for dinner and dancing. The time it took her to answer seemed like an eternity; although in reality was only a second or two.
"I'd love to."
