Journey Onward Ch. 03

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Jake meets Sandra.
5.4k words
4.35
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Part 3 of the 5 part series

Updated 06/07/2023
Created 12/11/2015
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csb1971
csb1971
5 Followers

Ok, readers...here's Chapter 3 of Journey Onward. I know it has been awhile since I've added a chapter, but hopefully the wait for Chapter 4 will be nowhere near as long. Speaking of Chapter 4, it will likely be the last chapter in this tale. As always I welcome your feedback and comments. Hope you enjoy!

*****

Jake stepped behind the woman pouring wine in the kitchen and placed his hands on her bare arms. She was startled for a moment, but after Jake gently kissed her exposed neck, she relaxed and continued to pour. He whispered, "do you have any idea how magnificent you look from behind?"

Sandra blushed as she finished pouring and turned around to face him. She reached up and pulled Jake's face down to meet hers and placed a kiss gently on his lips.

"You smooth talker. Keep that up, and we will see what happens."

*****

It had been an interesting few days for Jake leading up to that moment. He had created a profile on a dating website, and hadn't received very many responses. The free trial period had nearly come to an end, and he was considering scrapping the whole thing and going in a different direction to try to meet someone.

He'd been in his new surroundings for about 6 months, and was getting settled in nicely. Work was going well, he loved where he was living, and had acclimated to the weather. The one downside was a lack of a social life. Jake had always been a bit shy and reserved, so meeting new people, expanding his social circle, and more critically, dating was always a challenge. Once he got to know someone, he was sociable, but getting to that point was difficult.

During that time, he felt the grief and sadness over Kate's death begin to lift and heeding her wishes, began to think about exploring who might be out there for him. He had taken notice of some women at work, but was hesitant to pursue that avenue for a couple of reasons. One was that getting involved with someone you work with could backfire if things went south and the other was that he was considerably older than most of the people he worked with.

Jake had primarily dated and been with women older than him. He had no issue dating someone a few years younger, but most of the women at work were 15 to 20 years younger than him. He was old enough to be their father or uncle. While he would check out and admire these younger women, he chose for them to remain off limits to any potential advances from him.

There were some women closer to his age, only in fewer numbers. It did seem like most of them had wedding bands, though. He didn't want to go down that route, either. It usually was nothing but trouble that ended badly for everyone involved.

With those obstacles in place, he decided to cross work off of his list of potential places to meet someone. That didn't stop him from turning his flirtatious side on from time to time if he sensed that he was being flirted with. He chose, though, not to take things beyond that.

With work, then, being off limits, his other avenues were limited. He could frequent the bars, but he isn't much of a drinker and didn't want to spend the time or money. He thought about finding some social gathering or church or something on meetup.com to pass the time, but his shyness kept him from taking that leap.

That left online dating. It was how he met Kate, so it wasn't a foreign concept to him. It would allow him to screen potential dates from the safety of home, and perhaps eliminate some of the small talk that is common on first dates. He found a site that was running a special trial period and started to create his profile. He cringed at some of the questions, but filled it out anyway figuring the more info that was there, the less sifting through of random messages he'd have to do.

It took him awhile to go through it all and find a suitable picture to post. Once it was up and to his liking, he started to poke around the site to see what he might find. He quickly realized the pickings were slim. There seemed to be many more profiles of men than women, and those women on there were generally about the same age of those women at work. There were a handful of women that were his age, but none of them really stood out.

He stood up, sighed, and closed out of the site. He figured he had the free 30 day trial period to see what might pop up before he had to make any decision about whether or not to continue on. He wasn't feeling too optimistic based on what he had seen so far, but who knew what would happen.

A week had gone by, and Jake had almost forgotten about the dating site when he received an email saying that he had new matches. He logged in, and there indeed had been some new people who had created accounts. He read through them, and one or two of them caught his interest. He fired off a couple of emails to them to see what might happen.

The first woman was 42, blonde and recently divorced. It seemed like she and Jake had quite a bit in common, so he thought he would test the waters and see what happened.

The other woman was 48, brunette, and not so recently divorced. Her name was Sandra, and the more he read her profile, the more he was intrigued. She was into some similar things as he, such reading and writing as well as being a sports fan. The care with which she filled her profile out really interested him. Then, there was her picture. She was full figured, with an attractive round face, a great smile and dark brown hair. He felt an instant attraction to her. She seemed elegant. Combined with the text in the ad, he was very interested. He took the time to craft a heartfelt message to her and hit send with hopes that he'd hear back from her soon.

A day or so went by, and he heard from the blonde, Kelly. She thanked him for his email, but told him that she had already gotten back into a relationship with someone from another dating site so she was closing this account. Jake shrugged and decided it was not meant to be. He checked his outbox and saw that the email he sent to Sandra had been read, but he hadn't received a response yet. He was guessing that she had read it, and decided she wasn't interested so he moved on to looking through other profiles. Nothing grabbed his attention, and he decided to go do something more productive.

Two weeks had passed by, and he had loosened up a bit a work. He had been flirting some with another employee who had started at the same time as him. She was quite a bit younger, but there was an attraction there. They had talked about grabbing coffee sometime, but it hadn't happened yet primarily thanks to her busy schedule. Occasionally, they would see each other in the halls and talk for a minute or two, but that had been the extent of it. He stopped worrying about that and decided that if it happened, great, and if it didn't, he had someone at work he could be friendly with when they passed each other.

It was getting near the end of that 30-day trial period, and Jake made a note to go in and cancel the membership a day or two before. On a whim, he decided to log in and see if there was a way to cancel early. He was poking around the site to see if he could find any info, when he saw a message notification pop up saying he had new mail. He navigated over to the mail, and when he opened it, he saw a message from Sandra.

He perked up a little, and opened the message. She opened by apologizing profusely for not getting back to him sooner. She, like him, had only planned on being around for the free 30 days, and then completely forgot about it until she had logged in to see about cancelling it. She said that she had received a few messages, but that Jake's really caught her eye and she wanted to make sure she responded. He read through it, and a smile grew on his face. She seemed like someone he really wanted to meet and get to know. Plus, she was very attractive.

She closed the message by giving Jake her personal email address since she was closing the account down and wouldn't have access to the site anymore. Jake quickly copied that info down, and jumped over to his personal email and started typing a message to Sandra.

The next few days were a flurry of email messages sent back and forth getting to know one another with it ending in the agreement that they would go out on Saturday night for dinner. Sandra had lived in the area for years, and she knew of the perfect place off the beaten path where they could have a quiet dinner. She said she could come to him and leave her car and he could drive them there.

He had a hard time concentrating at work on Friday and was restless Friday night and for most of Saturday. She had told him this was a fairly casual place, so he decided on one of his golf shirts and a decent pair of slacks to wear. He looked at the clock and decided that it was late enough to finally start getting ready. He took his time showering and shaving. Once that was done, he gave his clothes a quick trip on the ironing board before heading into the living room to put some music on for when she arrived.

He took a look at the clock and saw that she should be getting there within the next 10 minutes or so. He tried to sit on the couch, but had too much nervous energy, so he got up and paced around some. On a lark, he decided to pull a couple of wine glasses down from the cabinet and got a nice bottle of red and set it on the kitchen counter in case things went well and she decided to come in after dinner. He mused it could also be used in case things didn't go so well, and he could drown his sorrows instead. He shook that thought out of his head and decided that he would be optimistic and would think about the positive option.

He heard a car pulling up, and looked out the window. He took a deep breath to calm the butterflies, and started towards the door. The doorbell rang just as he placed his hand on the knob to open it up. He opened the door and was momentarily left speechless.

Sandra stood in front of him in a sleeveless black dress that went down to right above her knees. She had a beautiful, full figured body with curves in all the right places. Her breasts appeared to be perfectly sized for her body, and her hips flared out causing the dress to expand with them. She had strong looking legs that ended in a pair of 3 inch heels. Jake drew in his breath to take a pause from looking at the rest of her, and looked into her waiting eyes.

He grinned sheepishly and said, "hi, I'm Jake," and reached a hand out to her.

"Oh, stop...no handshake here. We've been talking enough that I think I hug at the very least is in order."

Jake agreed and reached his arms out and took her into his embrace, pausing to give her a kiss on the cheek. He was amazed at how she fit in his arms. She was soft in all the right places as he felt her breasts press into his chest. He quickly realized that he should probably end this embrace before his quickly growing erection sprouted to full size.

They broke apart, and Sandra chuckled a little bit as they did and said, "it's been a very long time since I got that reaction out of a man."

Jake couldn't quite believe that and said, "I have a hard time believing that. You are incredibly sexy, and that hug was amazing."

"You are such a smooth talker, but sadly it is true. Knowing I can still cause that kind of reaction was a very pleasant realization. Thank you, Jake, for giving this old woman a cheap thrill."

"Stop...just stop. You are far from old and I stand firm on by belief that you are a sexy woman."

Sandra shook her head again, and said, "Enough of this. We need to get going to dinner. It has been awhile since I've been there, and I can't wait to share it with you."

Jake laughed and grabbed his car keys as they headed out the door. They walked down the walk to the car in the driveway, and he stopped for a moment to admire the view from behind. Sandra had a beautiful full, round ass that fit perfectly in her dress. The material hugged her cheeks and her hips as she walked forward, and Jake felt things stirring from below again.

Sandra ended his little reverie by saying, "Hey, did I lose you?"

"Nope, just stopped to admire the view. And what a view it is!"

That drew a snort from her followed by a rebuke. "You are incorrigible. What am I going to do with you?"

He laughed and ran ahead of Sandra to get the car door for her. That earned him a smile and a kiss on the cheek as she climbed into the car. "Such a gentleman. There may be hope for you yet!"

That got a laugh out of Jake as he got in and started the car. He had no idea where they were going, so he late Sandra do the navigating. After 20 minutes or so, they were pulling into the parking lot of a small restaurant that overlooked Lake Michigan. The time seemed to have gone quickly as they fell into easy conversation in between the directions to get to this place.

Jake got out of the car, and ran around to open up the door for Sandra. "This is beautiful. Until I came back here, I didn't realize how much I missed the lake. Thanks for choosing this place."

Sandra smiled up at him and said, "I figured this would be a hit for you. Sometimes I take the lake for granted, having been around here for so long. But, it is always a beautiful site. Now, come on. The food is as good as the view."

He doubted that a bit inwardly, but trusted her judgement and they went in.

She wasn't wrong. The meal was delicious and fresh with a great atmosphere. The time melted away as they talked through the entire meal about life, past experiences, and hopes for the future. Jake admitted that this was the first date he had been on since Kate's death where he was truly having a wonderful time and attributed that to the company. Sandra recounted that the last few years of her marriage were full of benign neglect and a lack of appreciation from her husband as well as a total absence of sex.

The meal was wrapping up and there was a pause in the conversation. Jake looked across the table and asked, "would you like to come back to my place to keep this going?"

"Well, I do have to go back there seeing as how my car is there, but I would love to come in for a bit to spend some more time with you."

With that said, Jake paid the bill and they were on the way back to his house. There was a building sense of anticipation in the car as they made the trip back. Both could feel it as they pulled into Jake's neighborhood and into the driveway.

He put the car in park, and went around to let Sandra out. Instead of backing away to let her get by, he pulled her into his arms as she got out of the car. He whispered, "I had a wonderful time tonight, and I'm excited to see where this will lead." He pulled her closer and planted a gentle, passionate kiss on her lips. He felt her melt into his arms as the kiss lingered. They reluctantly pulled apart and nothing more was said as they walked up to the front door hand in hand.

He opened the door, and followed her in and directed her down the hall. He said, "I need to step into the restroom for a moment. If you'd like, there's a bottle of wine with a couple of glasses in the kitchen."

"That sounds delightful. I'll get those poured while you do what you need to do."

Jake conducted his business, washed his hands, and headed back to the kitchen.

He stepped behind her in the kitchen and placed his hands on her bare arms. She was startled for a moment, but after Jake gently kissed her exposed neck, she relaxed and continued to pour. He whispered, "Do you have any idea how magnificent you look from behind?"

Sandra blushed as she finished pouring and turned around to face him. She reached up and pulled Jake's face down to meet hers and placed a kiss gently on his lips.

"You smooth talker. Keep that up, and we will see what happens."

He searched out for her lips again, and continued to kiss. The wine was momentarily forgotten as the kiss became more intense and passionate. Sandra's breasts were pressing into Jake's chest, as her thigh made its way between Jake's legs. His quickly growing erection was easily felt through the layers of clothes between them.

Sandra came up for air. "Whew...that's hot. I need to cool down for a second."

"Let's take these glasses into the living room and sit on the couch for a bit. We can unwind and see where things go."

She thought that sounded like a good idea, and she let him lead the way in. They kicked off their shoes as they settled into the couch. There wasn't much space between them as they picked up their conversation from before.

They slowly drank their wine as they related tales of their past and how they wound up where they were today. It was a bit of a contrast between Jake's tale of a love lost to death and Sandra's tale of a dying love. Both were lost souls searching for a connection, and at least on that night, it seems that connection was being made.

There was eventually a pause in the conversation, and they both realized that they had been talking for a couple of hours. Their wine glasses and the bottle were emptied and Sandra looked up into Jake's eyes. "I need to use the restroom, and then I should probably head home."

Jake was a bit disappointed, but understood that the night probably needed to come to a close. There was an attraction there, but he did not want to rush things. He did his best to not let the disappointment shine through, and directed her to the bathroom down the hall so she could take care of things.

He gathered up the glasses and the spent bottle and took them into the kitchen. He was optimistic that this could turn into something special. It had been a long time since he had felt like this, and he was enjoying it and hoping he didn't do anything stupid to mess things up. He was just finishing the clean up in the kitchen when he heard Sandra call him from down the hall.

He started down the hall and found her in the bathroom washing her hands. She looked up at him in the mirror as he stepped into the room and said, "Jake, I've had a wonderful time tonight. I don't want to screw things up here. I really like you and I feel like this could turn into something special."

"Sandra, I -"

"Hush...let me finish. I don't want to lose the courage I have to say what I want to say. What I want is to stay here with you tonight and have you make love to me."

Jake was taken aback by the admission. He had assumed that this would be a slow courtship that would work up to this.

She found his eyes in the mirror as she finished washing and looked crestfallen. "You don't want that, do you? Dammit...me and my big mouth."

Jake stepped forward and placed his arms around her. "Sandra, sweetheart. I want that so much. It just surprised me when you said it. I have been craving you since the minute I saw you tonight. I just assumed that you wanted to move slowly, and I didn't want to fuck things up by moving too fast."

"I thought I wanted to move slowly. It's been a long time since I've been with a man, and I was burned with my marriage. But, the more the evening went on, the more I realized that I really want to be with you tonight and see where things go. So, before I lose my nerve, I'm going to say it again. Jake, I want to stay the night and make love with you."

Jake still had her in his arms, with his chest to her back. He bent down and gently kissed her neck while pulling her closer to him. She closed her eyes and with a deep sigh, leaned her head back to give him better access. After a minute or two of this, Jake stepped back. Sandra started to protest, but quieted when she realized that he was unzipping her dress for her.

Jake took his time sliding the zipper down the dress, admiring her exposed back. When he got to the bottom of the zipper, he reached his hands back up to her shoulders, and slowly pushed the dress off of them. She gasped as she felt his hands on her bare shoulders, which were quickly replaced by the soft touch of his lips kissing her there. She let out a muffled groan as the dress slid down to her waist and Jake continued kissing her shoulders and the back of her neck.

csb1971
csb1971
5 Followers
12