A Little Story about Jack and Diane Pt. 02

A special thanks to Leslie Jones for her editing and feedback.

I had hoped to have this done much earlier, but two days after posting part 1, my wife was diagnosed with breast cancer. Thankfully it was caught very early and the prognosis is very, very good. For obvious reasons our lives have been turned upside down as we adjust to the new normal of doctor visits, treatment and other appointments every week.

I worked on this as time and drive allowed and am very surprised that the direction the story has changed considerably from what I had originally conceived. I'm not from the 'Once a cheater, Always a Cheater' camp. I think under the right (or wrong) conditions some people will yield to temptation and when faced with the possible consequences afterwards, will see their mistake, learn from it, and never make the same mistake again. That's how we learn...it's how I learned not to touch a hot stove when I was 4 years old!

I also believe that compassion and forgiveness (when warranted) are among the greatest of human traits and are a sign of strength, not weakness.

If you're looking for a BTB story then I would suggest you find something else to read. I am open to constructive criticism, but if you're going to be rude or ignorant and hide behind anonymity, expect your worthless blathering to be deleted.

If you choose to continue past this point, I hope you enjoy what I have written; I have certainly enjoyed writing it!

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A Little Story About Jack and Diane, Pt.2

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Diane was gob smacked; she stared at Jack for a moment as if he had just uttered incomprehensible nonsense.

"What?" She finally managed to say. "You can't be serious! Where the hell did you get an idea like that? I have never told you any such thing in my life, EVER! If this is some kind of sick, twisted joke, you need to stop now."

In a pleading tone, sounding almost like she was about to cry, she continued, "Jack, if you're doing this just to get me to listen to what you want to talk about, it's worked, OK? I'm listening! Let's talk about our intimacy issues, let's talk about what we need to do to fix things, but please, drop this nonsense about having an affair, I know nothing good could come of it. I know the kind of man you are and I know it would kill you inside if you went through with it...it would kill US!"

Jack carefully regarded Diane for a moment, observing and analyzing all the details.

He heard the hurt and fear in her voice, he saw the distress his words had caused, the quickening of her breath, the trembling of her voice, her eyes on the verge of tears. He saw it all and, for the briefest moment, considered taking this whole thing in a completely different direction. He had gone over this moment a thousand times in his mind, but it couldn't fully prepare him for the reality of the situation. It would be easy to stop now, to not continue down this path that he knew would break her heart...and his too, but he loved her too much for that.

With a loud sigh, Jack let out the breath he didn't realize he was holding. "You're right Diane; I did want to shock you. I wanted you to feel a little of what I have been feeling for the last couple of weeks so that we can see if this is something we can or want to work through."

Reaching over to the seat next to him, Jack picked up the television remote and pressed one of the buttons as he said: "And you're also right in that you never told ME that having an affair would be a way to get my sexual needs fulfilled."

The romantic music that had been playing on the television suddenly cut off and was replaced with the voice of Jill Ackman, Diane's very best friend since childhood.

"Diane, you can't be serious! What in the hell were you thinking?"

In a sorrowful voice Diane responded, "I don't know, Jill, I don't know. I didn't mean for it to happen, it just...happened."

"Damn Diane, this is really messed up. Never in a million years did I think you could do something like this."

"I know, Jill, I fucked up so bad, what am I going to do?"

Diane's head whipped around, looking for the source of Jill's voice. As her eyes focused on the television, she saw the words of their conversation displayed on the screen as if it were the transcript of an emergency 911 call.

Her hands shot up to her mouth as she cried out "No,no,no,no,no, oh god No! Jack, turn it off, please turn it off! Oh god, turn it off!" she wailed.

Diane jumped as Jack slapped his hand down hard on the table, rattling the plates and utensils. She brought her hands up to her face as she bowed her head and broke down, sobbing "Please, Jack, nooo..."

Jack turned up the volume to drown out Diane's sobbing.

"I don't know, Diane, I just don't know. Tell me everything that happened and let's see if we can sort this out."

As the playback continued, Diane's thoughts went back to the events leading up to her call with Jill.

--Diane's story--

Diane's company worked with the local college to bring in some business major students each summer for an 8-week internship. The interns would rotate every two weeks to each of the company's four main departments: administration, finance, marketing, and sales. It was on the fourth rotation that Tyler joined in the finance department where Diane worked as the assistant to the Chief Financial Officer.

As Tyler was introduced to the team, Diane took a few moments to appraise him.

He was attractive in a 'cute guy nextdoor' way. He was tall, maybe 6'-4", and he had a nice strong build, like he had grown up working hard or playing sports. He had an open and honest face, a nice smile, warm hazel eyes and a relaxed friendly attitude. He was the type of person who was immediately liked by almost everyone.

Diane was thankful that Tyler seemed to be a nice guy since she would be working with him quite a bit over the next two weeks to prepare the fiscal year-end reports needed for the upcoming board and investors meetings. Printing, collating, and binding the 450 reports that were needed was a lot of work and Diane was thankful she would not have to do it all by herself. Putting together the financial reports was Diane's least favorite job and she liked to get it done as quickly as possible. Since she could only spare about an hour each day to work on the reports, so she had to make the most of her time.

Eliminating the myriad of interruptions she typically had each day was paramount, so for the last couple of years Diane had taken to using the large archive/storage room in the basement. It was a large, well-lit room with several large tables she could use to collate all of the various documents for the reports, and most importantly, there were no disruptions - no one ever came down to the storage room!

Because Tyler was there to learn all of the various aspects of the financial department, it was decided that he would assist Diane with the reports for the last hour of each day. Diane was a meticulous planner, so she spent the first day explaining to Tyler her process for putting together the reports, making sure he understood each step and why they were doing it that way. Having to go back and fix 450 reports because of a miscommunication was certainly NOT an option!

Tyler proved to be very adept and needed little instruction as they worked on the reports each day. Diane found Tyler very easy to talk to and he seemed to enjoy telling her about his school, family, friends and hobbies. He didn't talk about any girlfriends or such which was fine with Diane as she didn't think a young man talking to an older female coworker about such things was appropriate.

On the third day that they were working together, Diane noticed several times that Tyler seemed to be staring at her and would quickly look away if she happened to catch his eye. She didn't think much of it except that the last time it happened, she noticed that Tyler was doing his best to hide an erection! Although she felt a little embarrassed, Diane also found it very flattering when she considered that a handsome young man like Tyler seemed to find her attractive.

Turning 50 last year had been very hard on Diane. Like many women that reach that age, she felt like her best years were now behind her. Although she didn't doubt for a single minute that Jack loved her every bit as much as she loved him, she didn't think that Jack still found her desirable. He was every bit as loving as he'd always been, but he never came on to her anymore the way he had when they were younger.

While Diane never once considered being unfaithful to Jack, it really gave her a thrill and a bit of an ego boost that Tyler seemed to find her attractive.

For the rest of the week she dressed in outfits that accentuated her shape and maybe showed a little more cleavage than she normally would. It was certainly nothing that would be considered unprofessional, just enough to maybe give Tyler a little more to look at. Maybe a little more to fuel his imagination at night, she thought, wondering if Tyler masturbated while thinking about her.

Over the next two days Diane observed Tyler out of the corners of her eyes and several times noticed him staring intently at her ass or her breasts. The one time she even caught him adjusting his pants to hide his erection.

Diane was really enjoying feeling sexually attractive again, and if she was being honest with herself, she was even a little turned on. She found herself leaning over a little more to give Tyler a better view down her blouse and even intentionally dropped a folder once as she walked by him, just so she could bend over to pick it up.

All too soon it was Friday and the workday was over. As Diane and Tyler walked up the stairs to the main floor, she told him what a wonderful job he had done all week, how much she enjoyed working with him and appreciated his help. Tyler responded that it was the best week of his internship so far and that he was looking forward to finishing up the reports with her next week.

They wished each other a pleasant weekend as they parted ways, Diane heading for her office to get her purse and cellphone while Tyler walked out the front doors. She thought about Tyler on the drive home and, while she was a little ashamed of how she had behaved around him, she was flush with the excitement of being found attractive once again.

She thought about Tyler frequently over the weekend, so much so that Jack had asked her why she seemed so distracted. Diane played it off, telling Jack she was thinking about everything she needed to do to finish up the fiscal reports for the big meetings at the end of the next week. She felt guilty for lying to Jack, but she certainly couldn't tell him she was thinking about a young guy in her office that seemed to be really attracted to her.

Sunday evening Diane laid out her work outfits for the week as she usually did. She savored the thought of Tyler admiring her figure as she picked out her clothes, so she purposefully picked out the business suits that she looked the best in.

Diane was conservative with her wardrobe; her clothing was always well made and fashionable but never anything that pushed the boundaries of acceptable business attire. This included her undergarments as well, fashionable and comfortable - no thongs or lace pushup bras for her! As she decided on which outfit to wear each day, she intentionally selected her best one for Thursday, the last day she would be working with Tyler.

After their usual Sunday evening routine Jack and Diane went to bed. As Diane drifted off to sleep, she thought about the week ahead, imagining how much Tyler would be turned on.

That night Diane had a dream that she and Jack were back at the island resort where they had celebrated their 25th wedding anniversary. They were making love in the missionary position, and she was urging Jack on as she built up to what felt like would the most intense orgasm she'd ever had. As she looked lovingly into Jacks eyes his face began to blur. She reached up to touch his cheek and her hand passed right through it, causing it to swirl around as if it was made of smoke. As she stared, the smoke coalesced and as the face came into focus, she saw it was Tyler, not Jack!

The shock of seeing Tyler's face brought her wide awake in an instant! As she lay there, trying to wrap her mind around what she had just dreamed, she realized she was actually quite turned on and very, very wet.

She quietly got out of bed, went to the bathroom, sat down on the toilet and masturbated; fantasizing that Tyler was on top of her making love to her. She had to bite her lip to keep from crying out as one of the strongest orgasms she'd ever had from masturbating overtook her.

Taking a few moments to come down from her orgasm, Diane cleaned herself up and climbed back into her bed. As she drifted back to sleep, she felt guilty for fantasizing about another man while masturbating, but justified it to herself by saying it was just a fantasy and men think about other women all the time when they masturbated.

Monday at work Diane spent the entire day in her office, thinking that not allowing Tyler to see her might increase his anticipation to see her. She went down to the basement workroom a few minutes early so that she would be able to see Tyler's reaction when walked into the workroom and saw her for the first time that day.

When Tyler walked in, Diane looked up from the worktable and greeted him warmly. She was happy to see Tyler seemed to spend a few extra moments checking her out as they exchanged pleasantries. As Diane looked at Tyler, last night's dream came to mind, and she found that she was becoming a little aroused.

As they continued their work on the reports, Diane became a little more daring and took several opportunities to position herself in a way to give Tyler a good look at her ass or down her blouse. Not wanting to embarrass him by 'catching' him staring at her, Diane instead focused on Tyler's pants, trying to gauge just how much he was being turned on. She wasn't disappointed, judging by the bulge in the front of his pants she had gotten him aroused quite a bit! This only increased her own arousal, making her quite wet by the time they were finished for the day.

Jack was working late every night that week so when she got home, she rushed up the stairs to her bedroom, hiked up her skirt and used her fingers to furiously masturbate her highly aroused pussy to climax while fantasizing about Tyler.

After she came down from her climax, Diane cleaned herself up, changed out of her work clothes and went down to the kitchen to prepare dinner.

As she prepared the meal her thoughts returned to Tyler and how much she enjoyed teasing him and, judging by his erections, just how much she was turning him on. Diane felt a familiar tingle and her pussy started getting wet once again! She couldn't believe that she was getting aroused after masturbating less than 30 minutes ago!

She quickly finished preparing the dinner, put it in the oven and then headed back up to her room. This time Diane went to the closet to retrieve her vibrator, stripped off all of her clothes and laid down on the bed.

She took her time, running the vibrator lightly across her breasts and pinching her nipples with her free hand, imagining it was Tyler licking and biting them. She continued pinching and pulling on her nipples as she trailed the vibrator down her body, fantasizing that Tyler was kissing his way down to her eagerly awaiting sex.

She spread her legs as she ran the tip of the vibrator all around the outside of her pussy before slipping it in the cleft formed by her plump outer labia.

There was a sharp intake of breath as she slowly slid the vibrator past her clit, plunged it into her soaking vagina, pulled it out and brought it back to her clit, smearing it with the juices that clung to the vibrator. She did this several times, working the vibrator deeper into her pussy each time until it was as deep as she could take it.

The fingers of her left hand trailed down her body and into her fat slit, finding her swollen clit. She alternated between circling her clit with her fingertips and stroking it up and down between her two fingers, all while continuing to work the vibrator in and out of her pussy with her right hand.

Diane took her time, savoring the illicit feelings as she fantasized about Tyler on top of her, plunging his cock into her as she built up to a massive orgasm. Almost without warning her hips started bucking up and down as she smashed her clit with her fingers while jamming the vibrator in as far as it would go. Her hips lifted one last time as she convulsed with the explosive release of her climax. Her fingers pressed down on her clit almost painfully as each convulsion sent a shockwave through her body.

Spent, Diane collapsed back into the bed as the convulsions subsided. Her hands dropped to her sides, allowing her pussy to push the vibrator out with the last of her contractions.

Diane lay there for several moments, unable to move, allowing her breath to return to normal. Feeling a tremendous amount of wetness between her legs, she gently probed her slit with her fingers and was surprised by the amount of her cream that covered them when she brought them up for inspection.

She reached between her legs and grabbed the vibrator as she sat up, noticing the copious amount her thick, white cum at the base of the vibrator as she turned it off. On shaky legs she made her way to the bathroom to get cleaned up. She felt a little guilty about having such a strong orgasm while fantasizing about Tyler, but assured herself that it was only to release her pent-up sexual needs, and that she loved Jack far too much to jeopardize their marriage by EVER taking it any further than that.

Jack arrived home a little before 8pm, they ate dinner and spent the evening talking about mundane things and watching some TV, just like they did most every night.

A couple of times throughout the evening Diane felt as if Jack was staring at her, but when she looked, he was clearly focused on the television. She figured her teasing and fantasizing about Tyler thought maybe she was just feeling a little bit paranoid.

At 10:30pm they went upstairs, going through their nightly rituals before climbing into bed and cuddling before going to sleep.

Diane felt a little guilty as she lay in Jack's arms; her head nestled against his chest. She loved Jack with her entire being and she felt like she was betraying him by fantasizing about Tyler. She knew without a doubt that Jack loved her as well, but it seemed that over the years Jack desire for her sexually dwindled to the point of being almost non-existent.

They still made love once or twice a month, but it was the kind of love making that comes from being married to someone for more than half of their lives...familiar and comfortable. It was a reaffirmation of their deep and abiding love, not the passionate love making of their younger days, oh how she missed that!

Growing up, Diane had always been self-conscious about her weight; she always compared herself to women that she felt had a better figure. But when she had met Jack, he had a way of making her feel like she was the sexiest, most desirable woman he'd ever met...even though she never actually believed it, she figured he just wanted to get into her pants. She supposed that was why she was playing this little game with Tyler, to relive the feeling of being desirable once again, even if it was only for a brief moment in time.

Tuesday and Wednesday were repeats of Monday. She knew that after Thursday she would likely never see Tyler again, so she wanted to make the most of her little game in the time she had left. Each day she went down to the work room before Tyler and adjusted her blouse to show off a little more cleavage when she would lean over the worktables. She even adjusted her bras so that the very top edge of her areola would be visible!