Chapter 1: Exploring New Territory

Jessica was a striking young woman in her early 20's when Tom first met her. She wasn't what you'd call "gorgeous" but she did have such an innate physical beauty that any man would notice her the first time he laid eyes on Jessica. The first time Jessica walked into Tom's place of business, he found himself inventing things that he could "show her" in order to spend as much time looking at her and being near her as possible.

There were several things about Jessica that were eye-catching and cock-hardening. One was her pretty face - very nice with full lips, pretty deep brown eyes and a nice complexion. Another significant feature about Jessica was her very long hair. Her light brown hair must reach down to at least her waist on her 5'8" or 5'9" frame. You don't see that many women with hair as long as Jessica's and on her it was totally sexy and hot. But, one of the most obvious qualities about Jessica that was impossible to ignore were her very prominent full breasts. Tom noticed that Jessica's tits must be at least D-cups and they were awesome on her otherwise rather petite frame.

The funny thing about Jessica is that she dresses in sort of an old-fashioned way with long skirts and sweaters that tend to disguise what lies underneath, but to a perceptive man who knows what he's looking for, there's no way of disguising what a sexy desirable body this babe has. The very first time Tom met her, she was wearing a long skirt and a blouse. Mmmmmmmm, boy, did that blouse fit nicely with her sexy big tits underneath. But during the summer, Jessica came to his workplace on one occasion wearing tight-fitting jeans and a T-shirt. Tom couldn't believe the hard-on he suddenly found beginning to tent his pants out very visibly and he hoped Jessica wasn't noticing the very physical effect she was having on him. Tom loved how different and how freshly sexual Jessica looked in this more casual outfit. He especially loved the way it was so obvious what kind of bra she had on and how the cups managed to shape around her full breasts contained within them. From the moment he first saw Jessica and what she was wearing, he knew his "next stop" had to be the boys' room where he could relieve himself by masturbating as soon as she left the store. The only thing he could think of as he stood there talking to Jessica and admiring the boldly sexy out-thrust of her tits in her tight-fitting T-shirt was what she must look like naked and waiting for her lover to join her in the bed. Tom found it difficult to carry on their conversation while his mind was reeling from the sexy images she was causing there.

Jessica's reason for coming to Tom's workplace permitted the two of them to establish a casual friendship that would require her to occasionally come back again for his help. He pinched himself at being the lucky man who was "customer-oriented" enough to make that first contact with Jessica and ensured that she'd come looking for him specifically whenever she needed assistance. He intended to give Jessica a lot more assistance in the days to come in certain areas of her life and experiences than she'd ever anticipated.

Tom finally decided to press things in a more intimate direction with Jessica by managing to offer to help her in her home with some of the research work and studying she was doing. Something had happened in Jessica's life during the summer that had really knocked the supports out from under her both mentally and emotionally. Tom found himself feeling sorry for the loss she'd experienced and even though she seemed to be handling it well, he could tell that she had suffered a serious psychological setback. Yeah, it was an "affair of the heart" and some jerky guy had hurt Jessica in a way that was so stupid on his part. But, it was to Tom's advantage that this other guy had blown it with her, and set her totally free again to make her own way in the world romantically.

The day before as Tom had been riding to work, he'd passed a place where he had accidentally met Jessica one morning. It was such a special occasion to actually get out of his car to buy a morning coffee, have the window in the next car roll down and find Jessica sitting there in a pretty business suit, greeting him unexpectedly as he headed into the store. They had talked briefly and then gone their separate ways. Tom hadn't seen Jessica again and the day before he'd found himself thinking about her and wondering what she was up to in the days since they'd last spoken.

Jessica had arranged a date and time for Tom to come to her home, and when he arrived at Jessica's, it was about 4:30 in the afternoon. She was living with her parents again after completing college and in anticipation of getting married in the months ahead. Since that hadn't happened, Jessica was still living with them while she looked for employment and what else she wanted to do with her life. He didn't know what to expect from their afternoon liaison but he found himself envisioning Jessica's legs spread widely apart as he bucked in and out of her pussy with his hard thick cock filling her over and over again.

Jessica met Tom at the door and was very cordial in trying to make him comfortable for their work session together. She was wearing a light brown button-up blouse and a pair of matching dark brown pants. Other than the time he'd seen her in those jeans and T-shirt, Tom realized he'd never really seen Jessica in very casual informal clothes. She fixed him some soft drink to quench his thirst and they quickly moved into her parents' dining room where she had all of her books, papers and drafts laid out so he could quickly survey what she'd been doing and where she still had much work left to be accomplished. Again Tom found himself struggling between genuinely giving Jessica the advice she needed to do her work while a huge part of his mind was just taking in what a sexy woman Jessica was and how aroused she made him feel. There had never been any overtly sexy comments made by Jessica, nothing other than a very attractive young woman who was very pleasant and eager to find what she needed.

After they had been working for about an hour, Jessica suggested they take a break and have a piece of homemade cherry pie and some fresh coffee she'd just perked. Tom readily agreed, hoping they could sit and eat where he could allow most of his attention to just look at Jessica and enjoy being with her. When Tom had finished his first coffee, he asked Jessica if he could help himself to another cup and she offered to get it for him. He insisted that she just let him wait on himself.

As Tom walked over to the kitchen counter, filling his coffee cup about 2/3 full, he noticed how Jessica had casually pinned her long hair up to keep it out of her face and so she didn't have to worry with it. As Tom walked back to his seat, he commented, "Jessica, I was so sorry to hear about your engagement falling through this summer. I was amazed at how well you took it but it sounded like that guy you were engaged to was a total jerk and didn't deserve to marry you in the first place."

Tom didn't know whether to expect Jessica to change the subject or if she would respond to his words of sympathy and encouragement. He was surprised when he heard what he had to say.

"Well, he thought he'd found other women who he preferred over me, so I gladly let him go once he told me that he had no intention of being faithful to our mutual commitment. It hurt very much at first. We'd been together for so long and I thought we were going to spend the rest of our lives happily together," Jessica said as he noticed that she was looking him straight in the eyes.

Tom decided to say exactly what he was thinking and see how Jessica would respond. "Jessica," he said, pausing to ensure he had her attention, "I think your former fiancée was a very stupid man. I can't imagine how any man would feel that there was another woman out there who would make him happier and be more fun to be with than you."

Instantly Tom noticed that tears began to form at the corners of Jessica's pretty brown eyes, and then began to spill down over her pale smooth cheeks. Tom found himself feeling guilty for bringing Jessica to tears but then he realized he'd fully intended to find her weak spot emotionally in order to wedge his foot into her life. Before he knew it, Jessica's tears were flowing freely as she suddenly opened up and began to admit how badly it had hurt when she'd found out her fiancée had been fucking some of the other women he'd been working with. She obviously couldn't believe that he would jump into bed with another woman while he was supposedly engaged to her.

Tom walked over to Jessica and stood there in front of her as he pulled her face against his body, holding her snugly there while the sobs of her crying became stronger and deeper. In a few moments, Tom took Jessica by the hand and led her into the family room of the house. He stood there in front of her and wrapped his arms around her, holding her shapely body close to his. He knew he had a sizable hardon in his pants and he hoped Jessica couldn't feel it pressing against her at that moment.

Then, Tom reached down in front of Jessica's body, closing his left hand firmly over the cone of her breast, feeling the material of her bra that encased it underneath the material of her blouse. The feel of his hand on her breast caught Jessica completely off-guard and he could hear in the moan which came from her lips both an awareness of how good it felt for a man to touch her and a pulling back as though she didn't welcome the intimate touch at all.

"Ohhh, Tom," Jessica said as she reached up and placed her hand over his that was covering her breast, hesitating as though she didn't know whether to remove it or press his hand more firmly against her body. Jessica had never really allowed any man to touch her in an intimate physical way, not even her fiancée. He had always said it was no problem that she didn't permit him to feel her breasts, her hips, and certainly not to take her clothes off and make love to her. But it had eaten at him until her fiancée had decided to break their commitment and enjoy the physical pleasures of other young women who were horny, lusty and more than ready to fuck him.