Watching Jennifer (closed)

[Sidney_1]

Hmm, that was odd, Jenn thought to herself. He sure did skedaddle after she turned down his major offer. Oh well. Men were tough to read.

Jen eventually went inside, took a shower, and made social plans with her friends at their houses. Just a pizza and catch up. Maybe go out for music.

Maybe she’d see Matt later in the week.

 

[Inspirinious]

Sunday morning had become the time each week that Matt visited the grave of his wife, Barbara. This particular morning he needed to discuss with her his own future, moving on with his life, and the guilt he might feel if he tried to love another woman. In the past, he would sit by her grave and talk out loud to her, and he could hear her voice replying, in his head.

This morning he was surprised that she began the conversation. "Matt," he could hear Barbara's voice in his head, "I know why you are here today. You are a wonderful man, you were a wonderful, loving husband, and you deserve the happiness that can only come from the physical love of another person. We loved each other so much, and I know you will always remember me. But you have grieved me long enough. It is time to find another person to share your life, someone you can love who will love you as much as I did."

Matt sat in silence thinking about Barbara's message, waiting for more. There was no more. Barbara had spoken one last time from the grave and had given him clear directions. That was so like her, he knew.

Standing, Matt had a few final words over Barbara's grave. "Thank you Barbara. You know I will love you always."

He walked away, and returned home.


Later that night, after the sun had set, Matt sat in his office by the large picture window and stared out over the valley below. The lights of the houses twinkled. The stars above twinkled as they always had. Matt needed something new. He looked down at the Ford's house next door, longing to catch a glimpse of Jenn.

But the window was dark. He sat and waited.

 

[Sidney_1]

Jennifer returned home around midnight to a quiet house. She grabbed some filtered water from the fridge, filled her glass, and then headed to her bathroom to get ready for bed.

After finishing her nightly routine, she put on a soft, thin white tank and some blue boy shorts. She glanced down at her toes and suddenly had the urge to listen to music and polish them in the moonlight by her window. In fact, she was going to ask her Dad if he could create a window seat for her tomorrow.

Jen streamed Vitamin String Quartet while she reviewed her colors—Espresso Yourself, Too Hot To Juggle Tamale, Sheer Fun, California Raspberry, And Hold Up Houston We have a Purple Sighting. Jen chose the new bright pink that she had just purchased- California Raspberry - and shook the bottle vigorously as she settled a chair, her water, and a magazine to rest her feet so she wouldn’t get polish on the window ledge.

She pushed back the curtains and opened the window. Tonight was warmer, but there was still a light breeze. Felt delicious on her skin as she polished her toes a bright, tropical pink. As she waited for the first layer to dry, she thought about Matt and hoped he’d find someone for his massive office project. She had felt badly saying ‘no’, but it was beyond her comfort level.

She made a mental note for her Mom to give him some contacts tomorrow. And then her mind wandered to the meticulous way he had applied the lotion, as if he wanted to memorize every moment and every nuance of her body. She realized that even if he felt attracted to her. . .well, she was young. . . she was in a bikini. . . she was next to him on a raft. . . it was probably natural for any male to react that way with a woman so close.

Jenn had just slimmed down a few pounds, but she knew she still had a voluptuous figure that caught the eyes of men when she ran in public. But, she had gotten so used to not really noticing. But, she had really enjoyed Matt’s touch, and began to wonder how it would feel again.

Her hands moved languorously over her exposed chest below her collar bone as she thought of him. What if she had been sunbathing nude? Would he have put lotion over her breasts? Would he have been equally as attentive and careful? Would he spend a little bit of extra time for his own lascivious pleasure or for hers? Her hands moved down to her full orbs, cupping them and squeezing them gently imagining the scene. She could see her erect nipples pushing against the thin, snug fabric. Mmmm.

Jen applied one more layer of polish and then fanned her legs in the cool air helping them to dry. She definitely felt horny now and she knew she’d be masturbating to the vision of Matt putting lotion on her bare breasts and bottom.

 

[Inspirinious]

Matt had sat in the dark for hours, watching the lights in the valley below and the sky above. About midnight his heart lept when the light came on in Jenn's room. From his vantage point, he had a clear view of her family's home, and a direct view of her window. 'Will she come to the window? Might she open the curtains?' he thought, he hoped.

And then she did both. He could see Jenn pull back the curtains, open the window and then she sat in a chair, in full view of Matt. She was only wearing a minimal amount of clothing, a tank top and some small, snug fitting shorts that allowed him to see her wondrous curves, and those great legs. Matt could feel his heart flutter, and his cock twitch. Yes, indeed, he had sexual thoughts about being with Jenn, and he no longer felt any guilt. Barabara had told him, in a clear voice, even if just in his head, that he should move on and find another woman to love.

As he watched Jenn, she appeared to be putting on a sensual show for him. Her hands ran over her body, and she cupped her breasts through the thin material of the top. His cock throbbed and he instinctively started to rub himself. It felt so good to have a sexual tingle flow out of his groin and wash through his body.

When she began to paint her toes, he was entranced by what appeared to be slow deliberate actions. 'Does she know I am watching? Could she be putting on a show for me?' he wondered.

Matt unzipped his shorts and pulled out his growing cock and slowly began stroking it while thinking of making love to Jenn. Yes, there it was in his head. A definite desire, a definite lust to have sex with this sexy young lady that lived next door.

'Does she know I am watching?' Again the question ran through his head. Maybe he should give her a sign. He reached over to the lamp and flicked the switch, turning it on, then off once. Then on and off a second time.

'Yes, that will be my signal to her that I am watching, two flashes of the light.'

 

[Sidney_1]

As Jennifer was fanning her legs to help the polish dry, she noticed a flickering of light in the distance. Her eye located the light at Matt’s house, a quick on and off. The light remained off and Jennifer assumed Matt had probably gone to sleep.

Hmm, that was weird. It was as if he was awake, then decided to go to sleep, and then a quick on/off of the light a second time. Suddenly Jen wondered if he had a clear view into her window! Perhaps Matt was trying to conceal that he had been watching her . . .or, did he want her to know that he was watching by signaling that he was home by having the light on?

Jennifer shook her head, wondering if she had had too long of a day of hiking, sun, and socializing. What a fantastical idea. . . that Matt would be watching her in her bedroom doing. . . nothing really…

As a test, Jen decided to moisturize her legs as thoroughly as Matt had applied the sunscreen earlier. She bent her foot towards her belly and began to moisturize her foot and then extended her leg upwards while the other leg was resting on the window ledge. Although she was dressed, if someone had been watching. . . perhaps with binoculars. . . they might be able to see what she was doing.

Once at the top of her thighs, Jennifer snuck her finger under the shorts and stroked her labial folds and clitoris lightly. She dipped her finger into her own fluids and then brought her finger to her mouth and tasted herself. Slightly salty, but otherwise tasteless.

Jennifer stood up, decided that she was being ridiculous, and closed the curtains.

As she went back to bed, she slid her boy shorts off, and aroused herself by imagining Matt lotioning up her naked body and brushing his erection near her juicy, vaginal entrance. Both of them so horny; and both of them knowing it was wrong for so many reasons. And Jenn let the fantasy stop there, as her fingers circled against her clitoris until she felt herself start to sweat and she knew her orgasm was close. “Oh, oh, mmmm,” she groaned, softly. “Yesss.. .” she sighed as her vagina and clitoris spasmed and she felt herself peak and rise, and then peak again, the spasming coming in waves. . . until she couldn’t take it anymore and she stopped touching herself.

Oh God, I have got to get a boyfriend soon, Jenn thought, as she wiped her juices with a tissue, and slipped her shorts back over her hips.

Relaxed and satisfied, Jenn fell asleep easily.

 

[Inspirinious]

Matt continued watching Jennifer, mesmerized by her every move, her every action. He continued to slowly stroke his cock. It felt so wonderful to watch her, and pleasure himself.

After pausing a moment, Jennifer began rubbing her legs, applying lotion Matt presumed. 'I should have binoculars to see her better.' he thought. He also knew that watching her this way was over the line, but he no longer could help himself. He was infatuated by her.

'Whoa, what was that? Did she just touch her pussy and then taste herself?' he wondered, filled with excitement as he stroked his cock even harder. With his free hand he unbuttoned his shirt, baring his chest for what he was about to do. He slumped down in the chair and beat his cock rapid and hard, the sexual intensity washed through his body. He closed his eyes and pictured his tongue on her sex, tasting her, pleasuring her.

He loved the taste of pussy and how his body reacted to that unique aroma, that unique taste. Eating pussy caused his whole body to tingle so intensely. He loved being that aroused, that horny. The resulting sex was always so intense.

Matt kept that image in his head and beat his cock so hard that the pain almost matched the pleasure.

Then he came. His cum shot time and time onto his bare chest. 'Ooooooh, so good.' he thought.

Matt then realized that this was the first time he had ejaculated, or had any form of sexual release, since Barbara died. It felt so intense, so fantastic, that he wanted more. He wanted Jennifer.

He looked out the window, down the hill to her bedroom and realized the curtains were closed, the lights were out, the show was over. He used tissues to clean up the wads of cum on his chest and then went to bed.

Matt wanted Jenn so badly, but he wanted to obtain her in the right manner, the gentlemanly way. He slipped into a gentle sleep with a smile on his face.

 

[Sidney_1]

Jenn woke up in a fit of inspiration. Logos! Why was she not creating monograms, logos, and personalized designs on the plain black and white cover-ups that everyone seemed to own? She could already imagine her own initials on the back of her bikini bottom, or on the upper left side by her hip. All of a sudden a flurry of ideas hit her. . . and she scrambled to find her moleskine in her purse.

Baldwin bounded into her room, sensing her excitement, and she pet him after finishing her notes.

“Let’s make some coffee! Did you miss me?” Jen said, playfully as she padded downstairs in her robe and let her dog out.

Her parents were already gone, but she had a feeling her Mom would be around. She had mentioned something about being in and out. Jenn couldn’t wait to share her ideas with her Mom. Plus, she needed her Mom’s help with the the graphics.

With a full mug of bold coffee, Jen headed back upstairs and showered quickly. She chose her favorite- of -the -moment- light blue lacy bra and a snug white tank with a pleated, thigh length navy skirt.

She texted her friends, notifying them of her arrival back in Boulder.

Hey, would any of you be interested in having any of your bikinis personalized with your initials or an original design? I got a great idea this morning! Let me know. Going to work on my red bikini. I’ll post on Instagram when I’m done. Dinner? Plans?

Jenn opened the curtains for light and worked the window open for air. She stuck her hair up in a messy bun, put on some Miles Davis, and began to work on some sketches of her initials.

After about an hour, she threw on her silver flats and decided to take Baldwin up for a walk by Matt’s house. They both needed a break.

 

[Inspirinious]

Matt began his Monday morning like most weekdays. Breakfast was relatively simple, yogurt with granola sprinkled on top, some fruit, (a banana this morning), and a cup of coffee while he read the news on his tablet. He was a news junkie and he read the news from multiple sources every day. In years past he got the news from the printed newspaper, but these days it was all digital. A tablet connected to the Internet gave him easy access to a whole world of information. Sometimes technology does make things much easier.

Another part of his morning routine, everyday except Sunday, was his daily run. He would run, jog, and walk 4 to 6 miles through the hills in and around his neighborhood. Fortunately there were enough flat roads that it was not too difficult. Where there were hills, he would walk up. Other wise he would keep a good pace with a brisk jog.

So this morning, like others, he put on his running shorts, a t-shirt, his running shoes, and off he went. Leaving the house, his course started by going up the hill.

Matt loved running as it was good for the muscles of his body - his legs, arms, and his heart. And it was also a time to cleanse his head before he began his work day. One of the roads that ran away from his neighborhood was relatively flat, running along the sides of the hills, and through the trees. He loved that route as it got him in touch with nature and away from the city. He appreciated the solitude, the silence, and the fresh air.

This morning he had done one of his long routes, nearly six miles. As his run was winding down, he slowed to a walk the last quarter mile as he approached his home. His chosen course allowed this last stretch to be the downhill approaching his home. He was soaked in sweat, a sign of a good workout. He checked his Fitbit for his heart-rate and it was good.

Looking up from his Fitbit, he saw Jenn walking towards him with Baldwin. She was a lovely vision in her white tank top, her short pleated skirt, and those marvelous legs. He smiled at her as they approached each other.

"Morning Jenn. Taking Baldwin out for a walk?" The question was more of a greeting than a real question as it was obvious what they were doing.

He bent down and petted Balwin. He was good friends with the dog from next door.

 

[Sidney_1]

“Hey Matt, yep. We both needed to get out of the house for a bit. Wow, you’re looking fit. It’s not easy to run around here. I’m impressed. How far and how often do you run?”

Jenn knew she could probably lose a few pounds from all the great NYC food. It was nothing overtly noticeable, but all of her clothes felt a little snugger than she would have preferred.

“I- I really should try to do more cardio, myself,” she said, patting her butt.

Jenn took in Matt’s sweaty form. He looked hot in more ways than one, she had to admit. She tried to shake the lascivious thought and not stare at his muscular thighs. It did feel . ... very grown-up to relate to Matt as an adult now. Or, near-adult. She still lived with her parents. But, it was fun to run into him independent of her parents.

 

[Inspirinious]

"I try to run every morning, Monday through Saturday, about this same time." As Matt spoke he smiled at Jenn as he was pleased that she continued the conversation. "I have various routes I take that range from four to six miles. Some are easier, some more difficult, especially because of the hills."

Matt tried to maintain eye contact with Jenn as he knew that was one way to better engage another person. He noticed that her eyes sometimes wandered. 'Even women can have elevator eyes.' he thought. His body tingled a bit from knowing that she appeared to be checking him out.

He did notice out of the corner of his eye that she patted her butt while mentioning cardio. He wondered whether their relationship could or would develop to the point that he could touch her in a sensual manner. Was she too young for him? She was now an adult. Would she consider some form of a relationship other than thinking of him as the guy next door?

"Maybe you would like to join me for a morning run? Great exercise and great cardio."

 

[Sidney_1]

“Matt, I think that would be great for me. And yes, I think I’d like to run with you on your easy route days. I don’t want you to have to slow it down for me. Although, I can hustle when I need to, so who knows what I’m capable of doing.”

Baldwin barked at a squirrel and pulled on his leash.

“I think he’s getting impatient. We should probably get moving. I’m sure you’d like to get home, too. So, just let me know when I can run with you. I’m looking forward to it.”

 

[Inspirinious]

"I should know later today what my schedule looks like for the next several days. I'll send you a text." Matt smiled at Jenn one more time as Baldwin pulled her away. He turned and walked towards his house.

After a good shower, Matt dressed casually in khaki pants, a polo shirt, and some comfortable loafers. He did not have any business meetings scheduled that day and would be working in his home offce.

The rest of the morning and most of the afternoon he worked on various architecture design projects. Besides the office build-out for Lockhart & Florrick, he also had been hired to design an upscale restaurant called Andersons that would be located in the first floor of another downtown office building. And he had agreed to design a home for one of the wealthist men in town, Frank Baker. He didn't normally take residential home design projects, but this was a very influential person and the project would help him establish ties to some very important business people in the community.

His work kept him busy, but he continued to have thoughts about Jenn. He had to admit that he was infatuated with her. He remembered how she looked earlier that morning in the tank top and skirt that accentuated her curves. She was cute, but that was a poor term to use for a woman. 'Cute' was often used to describe younger girls, not an adult woman and she was an adult woman. In his mind she was actually a great combination of youth, innocence, as well as an intelligent, beautiful, even a sexy woman with a great personality. 'Yes.' he thought 'Jenn is a wonderful woman."

Throughout the early afternoon he kept glancing out his picture window, looking down at the pool next door to see if he could catch a glimpse of Jenn sunbathing by the pool. But he never saw her.

By mid-afternoon his work schedule for the rest of the week had been finalized. He had a couple on lunch appointments, but nothing in the early morning or in the afternoon after 2. He would be free to go jogging any morning, and maybe Jenn would invite him back to her pool for another afternoon swim.

He sent her a text message.

"Jogging every day this week @ 8:30. Hope to see you."​

 

[Sidney_1]

Jenn was toiling away, forgetting completely about lunch, when she got Matt’s text. Just she and Matt. . . deliberately doing something together. It felt odd, but exciting.

I hope I can keep up with you. I’ll meet you at your place. I’ll be outside stretching at 08:25. Looking forward to testing my limits!

Jenn smiled at the idea of trying to keep up with super-fit Matt. Maybe this is just what she needed to lose those five to ten pounds. And then she noticed her hunger, and her parents arriving home and asking about dinner.

“Yeah, I’ll have a cheeseburger. Can you grill some veggies, too? I didn’t eat lunch,” Jenn yelled downstairs, to her dad.

Jenn thought about starting on some stitching. ..her initials JF. ..into her red suit with black thread. . . but, she knew she’d do a better job with a full stomach.

“I’ll throw a rice salad, together,” Jen offered, and thought about Matt. Was he eating alone every night? Maybe she’d make some dinner plans with him.

----

08:00 am

Jen awoke to her alarm and was grateful that her Mom had made some coffee. After grabbing a mug and a home-made muffin, Jen debated about what to wear for the run. Her shorts were snug and so were her tops. Oh well, she’d have to wear her stretchy biking shorts, a compression bra, and her college t-shirt. Anything else would look obscene. Jen put her hair into a high ponytail and then braided it so her hair wouldn’t blow into her face.

At 8:20am she headed to Matt’s place. She began to stretch her legs and hips on Matt’s front lawn, hoping he hadn’t forgotten about their running date.

 

[Inspirinious]

When Matt opened his front door and stepped out, he immediately saw Jenn on his front yard stretching before their run. A smile crossed his face. He was pleased that she would join him this morning. Although he usually preferred to run alone, being with her would be special.

As was his usual morning run attire, he wore running shorts, t-shirt, and his running shoes with socks. For longer runs he often carried some water. As he expected a shorter run this morning, he skipped the water.

"Good morning Jenn. Happy you could join me this morning. Looks like a wonderful day."

He joined her for some warmup exercises. Once they are ready, they headed up the hill.

"I usually start going uphill, so I walk until I reach the top. Then we can start jogging. I am thinking a shorter route to start with, just about 4 miles. How does that sound?"

 

[Sidney_1]

“Sounds great. I want a decent workout.”

Jenn was relieved to start with the slow upward walk. It actually felt great to stretch her legs. It was a good thing she had gone on the hike two days ago so she wasn’t totally deconditioned.

“So, how are your projects going?” Jenn asked, catching a sideways glance at Matt.

 

[Inspirinious]

"Several projects in the fire right now actually." Matt liked talking about his work. He enjoyed the work and it was fulfilling. He was glad whenever anyone else showed any interest.

"I've said a few things already about the office build-out for the law firm. In addition to that, I am making architectural designs for an upscale restaurant, and for a large residential home."

They were about half way to the top of the hill. Once there, they would pick up the pace to at least a jog which would make conversation more difficult. Matt had a few questions, so he spoke quickly.

"The restaurant will be a downtown location for Andersons, their second location in the city. While I am working on their project, they have offered me free meals at their current location. I hate eating out in nice restaurants alone. Might you consider dining out with me sometime and give an old man some company? This last part he said in jest as he didn't consider himself old, yet.

"And what are you doing this summer to pass the time? Any projects?"

They were near the top of the hill. If they wanted to keep the conversation going, they may have to keep the pace slow, but that would be acceptable to him.

 

[Sidney_1]

“A free meal at Anderson’s and your company? Hmm, let me think about it,” Jen joked. “Yes, of course I’d love to go out with you. As you know, the Fords have hearty appetites. I love a good meal.”

They were just about at the top of the hill and Jen tried to pick up the pace to ready herself for running.

“Well, I’m working on some design experiments and then I’ll probably sell some things on my online store. My Mom said she’d also employ me for some minor things, too. But, I’m going to fit in my personal time, as always. You know, some pool time, friends time, dinner time with you,” Jen winked.

“And if you don’t kill me. . . some running workouts and the usual physical fare like hiking and the health club for strength and yoga. I’ll probably treat myself to a few nice things, though – maybe a massage, a yoga retreat, a flight to NY to see my brother."

 

[Inspirinious]

"I don't intend to kill you. But we are here for exercise and fresh air. Shall we pick up the pace?"

Without waiting for an answer, he increased his own speed from a walk to a good jog. They were now on the ridge road which was fairly flat. He knew how far to go before cutting over to another road to return home that would make this a 4 mile course.

Jenn appeared to keep up the pace without any difficulty. He glanced over at her frequently, partly to judge her fitness for the pace, and partly because he enjoyed looking at her. Even in her workout clothes, and her hair up in a braided ponytail, she was still quite attractive.

He was pleased that she was already considering dinner time with him as part of her activities. He didn't want that to slip away, so he decided go ahead and ask her out.

"Are you available for dinner tonight? I would love to hear more about your design experiments, and about your brother. I haven't seen Jeff in quite a while."

 

[Sidney_1]

“Yes, I’d love to got out tonight. It’ll be fun to dress up. And sure, I can tell you about my silly ideas.”

The fresh air, birds, mountains, and trees brought a calm to Jen. Matt was going at the perfect pace, but she knew she wouldn’t be able to carry on much of a conversation. She was going to need to regulate her breathing. Fortunately, they were on a flat area.

“It’s lovely up here, I see why you like this route.”

 

[Inspirinious]

"I do love being out here. I love the serenity. A great way to start the day."

They jogged along in near silence for a while, the only sounds being their footfalls on the pavement, the birds in the trees, and their steady breathing.

Matt checked his heart rate on his Fitbit. He was doing fine, in a good zone.

Soon they reached the turnaround point for their run. Matt indicated to Jenn with his hand that they should take the next left which would be the way back home by a different route. Matt disliked retracing the same way he came.

As they turned, Jenn was slightly ahead of him. Matt enjoyed watching her backside as she ran, each step was so graceful. Catching up with Jenn, he ran next to her, side by side, their steps in sync. He watched her face, the regular breaths she took. She glanced at him, and he smiled back at her.

The sun was rising higher in the sky and they ran in more sunshine than shade. Matt could feel the temperature rising, his body working a bit harder, the sweat forming making his running outfit damp.

They continued on, side by side, step by step.

 

[Sidney_1]

Jenn was proud of herself for being able to keep up with Matt. He was quiet, so she was able to just lose herself in the moment and quiet her brain of all the people and friends that she should call and touch base with while she was in CO. She could feel the sweat on her forehead but the dry air and wind made helped it to evaporate.

By the last 1/8th of a mile, she and Matt slowed to a fast walk. She could feel her calves and thighs tensing up a bit, and she knew she’d have to stretch them out.

“Wow, that felt great. I guess I’m in better shape than I thought.”

Jenn looked down at her t-shirt. Sweat had soaked through her upper chest and the outline of her sports bra was pronounced. Fortunately, it had done a good job of compressing her breasts and minimizing the bounce.

Matt was sweating, too, but looked like he could have easily taken on another 4 miles.

“I can see why you like running. I just wouldn’t want to injure myself. So many runners end up with injuries.”

 

[Inspirinious]

Matt was pleased with the morning run. He had worked up a decent sweat, enough to indicate that he had given his body the workout he needed. Running with Jenn made it appear that the time passed so quickly. It seemed they had only begun, and then their time together was coming to a close so soon.

As they walked down the hill approaching their homes, he knew that this was not the best cool down for their muscles, the slope could allow muscles to tighten up. But they were almost there.

"Care to join me inside for something to drink? I have water, juices, and Gatorade." Matt paused a moment, and then continued "If you need to go, I understand. I hope we are still on for dinner tonight. Leave at 6?"

 

[DeadlySin27]

Removed

 

[Sidney_1]

Jennifer could feel her thighs and calves beginning to tighten with the downward descent. She had a feeling she’d be sore in a good way later.

“I’d love some water or juice. That felt great.”

Jenn was too embarrassed to admit that although the workout felt great mentally and physically, her legs were starting to feel a little crampy.

“And yes, dinner tonight. I’ll be over at 6pm. I’m looking forward to a delicious meal and delicious company,” Jenn said, surprising herself with the flirtation.

 

[Inspirinious]

Matt led Jenn into his home and back to the kitchen/breakfast area. She took a seat at the breakfast table while he set out two glasses along with pitchers of water, orange juice, and cranberry juice. He offered her to take whatever she liked.

He thought about what she had last said, "delicious meal and delicious company", knowing that she was referring to him, flirting with him. Was she just playing with him, or might she actually be attracted to him? He was rusty at the game, as he hadn't dated or flirted with a woman in 20 years. But he made an attempt.

"I am sure we will both consider dinner together to be quite delicious."

He poured himself a glass of cranberry juice and sat down across the table from Jenn.

"How are your legs doing? Walking downhill during cool-down can be tough on the leg muscles."