by Westside24

Copyright© 2016 by Westside24

Sex Story: It often doesn't happen that this is the first date ever for the person you are dating.

Caution: This Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   .

It was the best time of the year if you were a sports fan thought Jake. That was because the MLB season soon would be into the World Series while the NFL season was just starting and soon would be joined by the NHL and not much later the NBA. Spending his time watching sports on television was a nice way for Jason “Jake” Palmer to forget about work for a while.

Jake was a Senior Claim Analyst for a large insurance company. Watching sports enabled him to forget for a while the duties and challenges he constantly faced at work. These duties were different from he had when he was a Unit Claim Manager because there weren’t many personnel problems. He was starting to think more and more about asking for a buyout package and taking an early retirement. In five years he would be eligible to ask for the buyout and the more he thought about it, it seemed like that was what he was going to do.

He had been divorced for the past ten years and had no one to worry about except himself. His ex-wife Nancy was successful in her own right as an attorney. She wanted out of the marriage so badly that Jake received the townhome and most of their savings. That she remarried one year later wasn’t really a big surprise and told Jake she may not have been faithful to him as she should have been.

Over time the love making with Nancy had diminished to where it was less and less frequent. From what at one time was great had gone down to “Why bother.”

Grabbing a bag of chips and diet soda Jake sat down to watch the MLB game when his cellphone chimed.

Answering the phone he heard, “Jake Palmer, I am Paul Cousins, Mike Cousin’s brother.”

Jake had a close friend Tom Cousins and he knew Tom had a younger brother Paul.

“Yes this is Jake. Why are you calling Paul? Has something happened?

“Yes something has happened, Tom died.”

This was a big shock and Jake responded, “What happened?”

“He was found lying on the floor in his living room. They say it was a massive heart attack. The reason I am calling is that I heard the phone message you left him worrying about him not returning your calls. I found your name in the phonebook he kept.”

“You should know that he left me a letter saying that if something like that should happen he didn’t want any big funeral church service. He only wanted a small service at the funeral parlor for the family. Since he once said to me that you were a close friend I thought I would tell you that the service is tomorrow at ten.”

“Are you going to tell any other friends or just limit the service to the family?”

“Just the family.”

“Well I think there are some people that should be notified. Can you bring Tom’s telephone book and give it to me tomorrow? I will contact some of the people who I think would want to know of Tom’s passing.”

After ending the phone call Jake had time to think about his knowing Tom. He had first met Tom when Jake was hired at the insurance company to work in the claim department. Tom was assigned to train Jake. Over time they had become close friends.

At work a few years later Tom was accused of accepting kickbacks is settling some claims. It couldn’t be proven that he did that but it was enough to piss Tom off. He quit the company and in time became a very successful independent insurance sales agent.

Jake and Tom continued their friendship and would periodically meet over a few beers to discuss what was going on in their lives. Tom would relate that he was a successful skirt chaser and was not hesitant to go into the details of the relationships he had with various women. His descriptions of the sexual activity involving some of his conquests were quite vivid. Tom had never married and was constantly on the lookout for new female conquests.

Tom’s current squeeze for the past six months was Cindy Davis. Tom in talking about her to Jake described her love making ability by saying she was hotter than a firecracker and had the best body of anyone he had ever bedded. Jake had never met her and could only wonder what she looked like.

Jake was somewhat successful in his pursuit of the opposite sex but after listening to some of Tom’s exploits he thought his exploits couldn’t compare.

There was a small gathering of some fourteen people at the funeral parlor the next morning. It was a short service over a closed casket. Jake thanked Paul when he handed him Tom’s telephone book. Paul said he could keep it as he had no use for it. Jake left right after the service ended.

That evening Jake remembered he had the telephone book. He thumbed through it recognizing some of the names listed. There were a number of names he didn’t recognize but that was to be expected. What Jake found to be interesting was that next to some of the ladies names were anywhere from one to four stars. Jake could only assume Tom was in some manner rating these ladies. It was time to do what Jake said he would do.

He dialed the number for Wally Byrd who was listed as residing in Sedona, Arizona. Wally was a college roommate of Tom. Tom had stayed in contact with Wally and had visited him a few times during the years in the winter months. Needless to say Wally was shocked to hear the news as Jake relayed to him everything he knew about Tom’s demise. Wally thanked Jake for the sad news.

The next call Jake made was to Dennis Casey. Dennis for a time was a partner with Tom when he went into sales. When Dennis brought his son Mark into the business there was a personality conflict between him and Tom which caused Tom to split from Dennis and go out on his own. While he didn’t think it at the time he later admitted that it was the best thing he did as it resulted in Tom becoming a very successful insurance agent on his own.

Dennis’s reaction was similar to Wally’s and he thanked Jake for making the effort to contact him.

The only remaining person to contact was Cindy Davis. Jake noticed there were four stars next to her name. Before Jake made the call he closed his eyes and tried to remember everything Tom has said about Cindy. Other than her having supposedly a great body that was all Tom had said about her physically. Tom said she was divorced and fairly well to do. He ex-husband was a successful hedge fund manager. She had said the reason they divorced was that he was physically abusive to her.

Per Tom, Cindy was no dummy and was not about to take his abuse any longer. She purchased a number of nanny-spy cams and had them installed throughout her home. It didn’t take long after these devices were installed that they recorded her husband physically abusing her. What was an added bonus was that they also recorded him doing a number of things with his hedge fund that the SEC would take a dim view of.

Giving this information to her divorce attorney resulted in Cindy receiving a lucrative divorce settlement. She received the large house, the condo in Naples, FL, and a substantial portfolio of investments that would maintain the living style of comfort she had become accustomed to. In looking for something to do she became a part time realtor concentrating on the expensive homes owned by her country club acquaintances. She sold her house and purchased a condo.

With a little nervousness on his part Jake pressed her phone number into his cell phone. After three rings he heard, “Hello.”

“Cindy Davis?”


“Cindy you don’t know me but my name is Jake Palmer. I was a good friend of Tom Cousins.”

“Yes, Tom has mentioned you.”

“Well there is no easy way to say this but the reason I am calling is to tell you that Tom passed away.”

“Oh my God! What happened?”

Jake went on to explain the circumstances surrounding his death and the services that were held.

“It was just last week we were discussing plans to go to Naples in a couple of weeks. This has gotten me shaken up.”

“Well I wanted to let some of Tom’s friends know what had happened and if there is anything I can do for you please let me know.”

There was a pause in the conversation and then she said, “There is something you can do.”

“What is that?”

“Maybe we can get together and you can tell me more about Tom than I know. I thought he was a little guarded in telling me about himself.”

“Maybe you can tell me stories about Tom that I never knew either.”

Because of Jake’s work it was agreed that they would meet Saturday for lunch to have this discussion.

In waiting for Saturday to come Jake couldn’t help but wonder what Cindy looked like. Her voice on the phone was pleasant and somewhat interesting. He could hear a touch of class in her voice when she spoke. That she was the sexual dynamo Tom indicated she was gave him something else he wondered about.

At the agreed time Jake was sitting at a table in the restaurant watching its entrance door when he observed a single lady enter. She was of average height with dishwater shoulder length blond hair she wore in a ponytail. Facially she wasn’t what you would call beautiful but she was attractive. Her figure he could see was slim and trim with some nice size breasts that jiggled when she walked. She was looking at the patrons and a smile came to her face as she saw Jake waiving an arm at her.

Her walk to Jake’s table caused him to rise and gave him some first impressions. There was a classiness and confident style in her walk. The jiggle to her breasts indicated she was amply endowed. The dress she was wearing was expensive and did not just come off a rack.

Extending her hand to Jake she said, “You must be Jake. It nice to finally meet you as Tom did talk about you.”

“Nice meeting you too. Tom had said he was dating you but he didn’t say that much about you.”

Jake knew a lot about Cindy because of what Tom had said but Jake thought there was no reason to tell Cindy that he did. He would just wait to see what she said about herself.

At the table they perused the menu and asked the waitress to give them more time before they ordered. Cindy started the questioning asking about Tom and his history. Jake gave her the full story from when he met Tom till he received the phone call from Tom’s brother.

After they placed their food order Jake asked Cindy about her relationship with Tom, how they met and also about herself. She gave Jake what he would call was the condensed Readers Digest version which was fine with Jake as he knew considerably more about her than she related.

While they were talking Jake continued to get more impressions of Cindy. She seemed like a very nice person and was not enamored with herself. Her manner of speaking indicated she was well educated. From what she said he thought she was about eight years younger than him. He could only guess if she was as good of a lover as Tom said she was but something was telling him that she probably was.

The time just flew by and before he knew it, it was a two hour lunch.

In putting his credit card in the tray to pay the bill Jake said, “I really enjoyed talking to you today. I learned a few things about Tom that I didn’t know.”

“I enjoyed myself as well. There are a lot of things you told me about Tom that I didn’t know.”

“We maybe talked out about Tom but I would like to see you again. Would you like to go out to dinner next Saturday?”

There was a short hesitancy on Cindy’s part before she said, “Yes, that would be nice.”

She took out a business card and wrote her home address on the back agreeing to a six o’clock time.

Jake had some thoughts about Cindy during the week. One thought he had was wondering what Tom would say now that Jake had a date with Cindy. Knowing Tom as he thought he did, Jake thought that if Cindy was happy Tom would be happy.

It was a good dinner date with Cindy for a number of reasons. She was wearing a light green dress that was tight enough to show she did have an excellent body. Her intelligence was evident as she was able to give as well as take in their conversation. Couple that with a warm caring personality made for a great evening.

If there was one thing missing it was that the evening ended with Cindy leaving Jake’s car thanking him for a nice time. There was no good night kiss or invitation for him to come up to her condo. Maybe it was too soon for something to happen but this ending of the date was something that was on Jake’s mind.

Jake’s concern or worry about this lack of affection continued for the next two dates with Cindy as they both ended the same way. He knew he was attracted to her but it seemed that Cindy was not attracted to him. He thought he would give it one last try and if nothing happened, well there were other fish in the sea and he would turn his efforts to try and catch some of them.

He let a weekend pass without asking Cindy out to dinner. When he did call the following week she sounded a little surprised and at the same time glad he called. Instead of going out to a restaurant she suggested that she would make dinner for them at her condo.

At her condo Cindy seemed genuinely happy to see Jake. She looked good in the white blouse and loose checkered skirt she was wearing. The skirt gave a nice sway to her hips when she walked. The scent of the expensive perfume she was wearing was evident and a little intoxicating.

After they both had a dirty martini Cindy served dinner. The filet mignon, baked potato and asparagus with hollandaise made for an excellent meal. She was a good cook and he could tell she was pleased when he complimented her on her efforts.

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