Chapter 1: Exploring New Territory
Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Heterosexual, First, Oral Sex, Petting, Pregnancy, .
Desc: Sex Story: Chapter 1: Exploring New Territory - Jessica's new in town and she comes where Tom works looking for some information. The young couple hit it off right away and Jessica invites him to her home to do some work together.
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.
Suddenly Jessica decided not to force Tom to take his hand off her breast, instead she wrapped her hand over his, pulling it closer into her tit. At the instant Jessica made that decision, she suddenly realized that she was feeling very wet between her legs. She hadn't noticed anything in the way of sexual arousal earlier with Tom but the talk in the kitchen and then his touch on her breast just then had started a hot fire burning within her loins.
As Tom felt Jessica go with him in the passion of their touching, he allowed his body to press more firmly against hers, now permitting the fullness of his hard urgent erection to begin touching her body at the level of her pussy. Tom also took the hand that Jessica was pressing into her breast and began to rub it up and down over the nipple and tip of her breast, using the motion to caress and turn her on more, he hoped.
"No, Tom, please, no," Jessica moaned as she fought an overwhelming desire to let him know that she really wished at this moment that he would pick her up and carry her to the queen-sized bed in her own bedroom. Jessica felt urges and burning desires in her body that she'd only felt a couple of times before. She was scared of what she was feeling and yet she felt totally comfortable being alone with Tom and having him touching her the way he was.
Tom struggled with Jessica's "No" and yet her hand pulling his hand against her tit let him know that his advances were not totally unwelcome. Tom knew what he wanted to happen and he could feel that Jessica was tottering on the edge of wanting his advances and not wanting him to touch her intimately. He decided to press another step forward and see how the beautiful young woman responded.
Tom took his hand off of Jessica's hotly curving breast and reached up between their bodies to begin unbuttoning her blouse. He figured if she really didn't want him to go further, she'd definitely stop him when he began to remove her top.
Jessica had loved the feel of Tom's exploring hand over her breast and she'd noticed that her nipple had begun to harden and perk up it's little point from arousal as the strong warmth of his palm was closed over her breast. When she felt his hand come off her breast, she found herself wanting to grab it and place it back there again. But when she noticed that Tom was reaching up and beginning to unbutton her blouse, Jessica didn't know whether to give herself to him immediately or run away from this man who she'd really hardly knew.
Jessica fought within herself trying to decide what to do. Allow Tom to continue undressing her or firmly take his hands away from her blouse and tell him that she didn't welcome his advances. As Jessica stood there, allowing Tom to undo the top button and then a second and a third, she felt her pussy growing wet and a hot fire of desire for this virile young man's touch on her body. She felt herself feeling more alive than she'd felt in many months and she suddenly felt overwhelmed by the desire to let a man show her that he cared about her as an attractive young woman.
Then, Jessica did something that even surprised her with its boldness - she reached up to the buttons of her blouse that remained fastened and she began to undo them one by one for Tom herself. When she had them undone all the way down to her waist, Jessica pulled the blouse out of her pants and shrugged it off her shoulders, throwing it to the floor. Tom's breath caught when he saw how sexy Jessica's full mature breasts were in the bra she had holding her tits firmly. He reached up and placed a hand over both her breasts, feeling the cool firm flesh under his fingers and hearing Jessica's quickening breath escaping her lips as he touched her more boldly.
Tom led Jessica over to the nearby couch and he gently laid her onto her back as he knelt there on the floor beside her, leaning down to kiss her in the cleavage between her twin mounds. His left hand was touching Jessica's soft brown hair, allowing his fingers to caress it as his lips moved from her cleavage down over the peak of one of her bra-cupped tits. His other hand moved down over her naked belly, finding the waistband of her pants and then moving down over the lower belly, covering where he knew her pussy lay beneath her clothes.
Jessica lay there underneath Tom's touches, loving the feel of his lips on her breasts, in the cleavage and then on the peak of her tit. When she felt his hand move downward to her groin, however, Jessica found herself really panicking suddenly. Now she was further along in an intimate experience with a man than she had ever been before. She'd never gone this far with her fiancée and she'd never expected to until she was married. She'd never done this before and her she was lying on her parents' family room couch with Tom's hand touching her hotly between the legs.
Tom moved up toward Jessica's face, allowing his lips to close over hers in a kiss and then he broke the kiss, moving downward to reach under her back and undo her bra, allowing the cups to lie loosely on her breasts as he moved further and began unfastening Jessica's pants and pulling them down and off of her legs. Jessica lay there for only a moment, allowing Tom to continue undressing her and then she reached down, grabbed her pants by the waist and helped Tom remove them and throw them onto the floor beside the couch. She reached up, pulled her lacy beige bra off of her tits, throwing it onto the floor as well, and then she took Tom's hand and led it down in between her legs, helping him to feel her pussy and how moist she'd become since he'd first come into her house an hour or so earlier.
"Tom, I want you to make love to me," Jessica said in a voice that was somewhat quiet and unsure but her hand over his as he felt her brown-furred pussy let him know that she definitely was with him in what he wanted to do. Tom moved his hand underneath the yellow bikini pants Jessica was wearing and he allowed his finger to slide up and down the slippery crevice of her pussy lips. He loved how wet Jessica had gotten and then he curved one finger slightly, pressing it in between Jessica's cunt lips and diving deep inside her body.
"Mmmmmmmmmmmmmmm," Jessica moaned as she felt Tom's finger slipping inside her pussy. She'd only felt her own fingers in there before when she'd been rubbing her pussy and clit to help herself get off when she masturbated. It felt so wonderful to have a sexy man touching her and she felt her pussy gush wetness as she found herself burning with desire for Tom to have his way with her sexually.
Tom allowed his lips to settle over Jessica's sexy dark brown right nipple when her breasts were bared as she took her bra off for him. As his finger began to get wetter with Jessica's pussy juices, he fucked it in and out of her pussy more quickly, allowing his finger to dive inside her until he couldn't go any further. The rest of his fingers wrapped around the curve of her ass underneath her pussy and on a full inward stroke, he was actually raising Jessica's curved ass up off the couch. Jessica felt herself uncontrollably getting more aroused and wanting Tom to do anything and everything to her to bring her to a high level of sexual excitement and fulfillment. She suddenly felt herself feeling very wanton and very sensual as she moaned and began to move around on the couch underneath Tom's hot sexy touch.
Tom reached down, pulling Jessica's panties down over her long shapely legs, noticing how fluffy and full her dark brown pussy hair was when he pulled her panties away from her hips. Then, Tom grabbed Jessica's legs just above her ankles and rotated her legs out towards him where he could gain better access to her increasingly horny pussy. Tom wanted more than anything at that moment to slip in between Jessica's legs and slide his thick hard cock inside her pussy and fuck her. But before he did that, he intended to eat this sexy young brunette's pussy and at least get her ready to fuck. He might even be able to bring her to tan orgasm.
When Tom moved where he was comfortable to get in between Jessica's legs, he spread them so he could reach her pussy. Tom felt his cock throb hotly as he loved how sexy Jessica brown pussy fur looked. He could already see that the lips of her cunt were swollen and wet from her being turned on and he dipped a finger in between the lips of her pussy again before he leaned his face down close and flicked his tongue out over the hardening nib of her clitoris. "Ohhhhhhhhhhhhhhh, yessssssssssss," Jessica encouraged Tom to lick and touch her in her most intimate parts. She'd never felt the touch of a man's mouth on her pussy and this was something she could never have even imagined. Tom began licking and sucking on Jessica's wet pussy and her aroused clit, then he cupped her twin asscheeks in his hands as he buried his face hotly in the middle of her thighs. His tongue dove inside Jessica's pussy again and again, making her hotter and hornier than she had ever felt before in her 20-something years of living.
Jessica's hands came down on the top of his head, and she pressed firmly against him, thrusting her groin up into his licking, kissing mouth as her hands firmly encouraged him to do whatever he wanted with her pussy. Tom wanted to caress and play with Jessica's tits and hair and all of her body but for the moment he could only concentrate on her cunt. He licked and sucked her clit and her pussy until he could feel her wetness increasing and her hips were bucking her ass up off the couch to meet his face. Suddenly Tom heard Jessica moaning and he knew he'd achieved his goal - he was about to bring Jessica to a strong lusty orgasm. He continued licking and then probing his finger in and out of Jessica's tight pussy until he heard her moaning "yeesssssss, yes, ohhhhhhhhhhhhhh,, mmmmmmmmmm" until he heard her sighs and moans begin to taper off and he knew that she'd moved through her climax and was ready - more than ready - for Tom to make his next move with her.