Looking Back
Chapter 1

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

Desc: Romantic Sex Story: Chapter 1 - If a man limits himself to only getting involved with women of a certain age group he can be missing out on some interesting situations.

Sitting on his home’s patio, overlooking the second fairway in this golf course community, Kevin Williams was very content with his life. Sipping on a soda, he thought that the past twenty years since he graduated from college had gone by in the blink of an eye. He did admit to himself that it had been financially rewarding and that he did have an interesting social life. He fondly remembered a number of things that had happened during those years as he reminisced about his life.

Kevin graduated with a business degree, but he wasn’t quite sure what he was going to do with it. The interviews with the recruiters on campus weren’t that productive. His father had talked about investing money in the stock market and this pushed Kevin to accepting a job offer that what was called a ‘stockbroker’ back then. The designation was later changed to that of a ‘Financial Advisor’ by his firm. He had secured his broker’s license, and with some additional schooling, received the designation of ‘Certified Financial Planner’.

This career was not what one would call financially rewarding initially. Finding customers was difficult and never ending as he tried to increase his number of clients. After a few years, he seriously considered whether or not this work was what he wanted to do for the rest of his life. He enjoyed selecting stocks to invest in and was fairly successful in doing that, but he knew he had to increase his client list if he was going to achieve the monetary success that he was seeking.

While contemplating if this was what he wanted to do in life, he concluded that what he needed to do to increase his client base was to ‘follow the money’. But where was the money was, is the question that he constantly pondered.

It was after reading a column in the newspaper about investing for retirees that he concluded that’s where the money was. He needed to be in touch with these workers before they retired and they received in some cases large sums of money. Taking a business directory out, he called the larger corporations in the area and asked to speak with the Human Resources Manager. When that person was on the line, Kevin asked if they were holding any training seminars for their employees that would be retiring in the near future. Most of the HR Managers said that they weren’t and asked Kevin to explain what he was inquiring about or suggesting.

Off the top of his head Kevin went on to say that these people who were retiring were facing a big change in their lifestyle and one that some of them were not prepared to handle. A day’s training session for these employees and spouses could consist of someone from Social Security talking about what the person could expect from them as well as what the Medicare benefits and costs were. Maybe someone from the HR department could talk about what the pension options and what the retirement benefits would be. There could also be someone from the medical profession talking about senior healthcare. Finally, someone like Kevin could talk about investing, since most of the employees had 401Ks. Some companies who offered the employees pensions offered them the option of electing to receive what the cost of an annuity would be in a lump sum to purchase a pension in the amount of monthly benefits the retirees were entitled to. Kevin pointed out that this could be a considerable amount of money that some retirees were ill equipped to handle and invest those funds. Those retirees who received their 401K funds or opted for the lump sum needed to convert these funds they were receiving to generate income which needed to last them for the rest of their lives.

He thanked the HR managers for their time and said he would send a follow-up letter outlining what they had just discussed. He asked that if they did do these pre-retirement seminars, he hoped they would consider asking him to do the portion that covered investing. He assured them he would cover the subject adequately in the time allowed and wouldn’t turn it in to a sales pitch for him to become the retirees’ financial advisor.

Kevin thought that if he did the presentation correctly and pointed out the many intricacies and pitfalls of investing, a number of the retirees would become his clients as they realized the need for and may not be aware of any other financial advisors.

It was about three weeks after Kevin started making these phone calls and sending his letters out to these corporations when he received a phone call.

“This is Pamela Harrison from the New-West Mutual Insurance Company. I am the HR manager of our regional office here. We have considered your suggestion about pre-retirement seminars and have concluded that it is a good idea and something we should be doing. We will be having our first seminar in two weeks and are asking you to participate. Can you attend this seminar?”

Kevin listened to her talk and enjoyed hearing her very pleasant and professional voice. He wondered what she looked like.

“I will be there and thank you for the invitation. Will you be in attendance?”

“Oh, I still have some years to go before I retire, but yes, I will be there to see if this is something the employees enjoy and something we should consider doing on a regular basis.”

Pamela gave him the specifics as to location and time and ended the phone call.

Kevin spent sometime on putting an outline together on what subjects he would speak on as well has making up some slides to go in his power point presentation. He also gathered up some brochures from his firm about retiring and stapled his business card into these brochures.

Kevin’s social life at that point was not that great in how it pertained to the opposite sex. He did date and at times was successful if the measurement was how often he bedded his dates. In spite of that he felt something was missing but he didn’t quite know what ii was.

The two weeks had quickly gone by and now he found himself walking into an outlying claims office of this insurance company where the retirement seminar was being held. Kevin was scheduled to put his two hour presentation on at two thirty. The seminar had started at nine that morning. The receptionist directed him to the conference room and in entering he could see the people there were on a coffee break.

He was a little lost as to what he should do but an attractive lady in an expensive dark business suit walked up him.

She extended her hand to him and said, “Kevin Williams? I’m Pamela Harrison. I want to thank you for coming here today. This break will be over in about ten minutes and I will introduce you. Is there anything you need to make your presentation?”

“No, I see you have the equipment I need to plug in my computer into to do my power point presentation. I don’t know if I will use the blackboard here but I may. I would appreciate it if someone could hand these brochures out when I start my presentation. I can introduce myself to the group when we start or you can if you wish to. Here is a short resume on me.”

Pamela said she would introduce him and studied his resume.

Kevin went to the front of the room and started to organize himself for the presentation. While he was doing this and later in watching Pamela do his introduction, he had some nice thoughts about her. In her heels she was about five feet nine inches tall, maybe about one hundred and thirty five pounds. She had short auburn hair and a very nice figure from what he could see. Her breast size was hidden somewhat by her suit jacket, but she did have a nice bottom the jacket couldn’t hide, along with slim calves and ankles. Age-wise, she was probably a good ten years older than him, but that was a non-factor as far has he was concerned. He wondered how good of a lover she would be.

His thoughts about her ended when in concluding her introduction he heard her say, “I took a quick look at what the total of the your 401Ks and if all of the twenty eight of you soon to be retirees were to take your pensions in a lump sum what that amount would be. That total comes out to approximately nineteen million dollars. That is a lot of money and to talk about how to handle it we have invited Kevin Williams. He will address those issues as well as discuss things you need to consider in investing those funds.

Kevin rose to some applause and proceeded to give his presentation. He talked about risk and return, listing the safest investment for income to the least safe. Laddering of bonds was discussed, along with examples and results. Stocks and the need for them to offset inflation with the increasing life expectancy along with the rise in Dow Jones over the years were discussed. The need for diversification and asset allocation as well as what the retirees could reasonably expect in the way of returns was the last topic he covered.

He concluded his presentation by telling them not to be greedy or make mistakes in chasing what is hot in the market to increase their rate of return. The “If it sounds too good to be true, it probably isn’t true” axiom was followed by him saying, “It is very important that you don’t make mistakes in handling these funds. I wish you success if you are going to do the investing on your own, but consider getting professional help in managing this money if you feel you don’t have that ability to do it by yourself. I can’t emphasize enough that you can’t afford to make a mistake in handling those funds.”

He received a nice round of applause as he concluded. A number of people came up to Kevin with some questions afterwards, and asked if they could talk to him in depth about investing. He told them that his contact information was in the brochures and encouraged them to contact him.

Pamela came up to him after most of the people had left and thanked him for his presentation.

“I thought it was very informative, and I learned a few things myself. It gave me something to think about as to my individual investments. I will say that you didn’t directly solicit any business, but I wouldn’t be surprised if some of these people contacted you to handle their investments.”

‘Well, that’s the business I’m in and I would be less than honest if I said I wasn’t hoping that they will contact me. I hope I have given them something to think about in handling these funds. I do want to thank you for giving me the opportunity to address them. I was wondering, since it is late in the day, if I could treat you to an early dinner as my way of saying thanks for this opportunity. If that presents a problem because of you having to do something or having a significant other just say no.”

Kevin could see that Pamela was a little taken back by his dinner invitation but she recovered well.

“No, there is no problem. We could go to dinner in this area and I could let traffic clear out and not have to fight it too much on my trip home.”

He thought it would be an enjoyable dinner and it was. Pam was a very interesting person for a number of reasons. First of all, she was highly intelligent and a good conversationalist. She, without mentioning names, was not reluctant to talk about the hot topics at work. Equal pay and sexual harassment were hot button issues in the HRS department. She did volunteer that she had been divorced for ten years and asked Kevin about his status. He informed her that he was single.

Kevin still wondered how she would be in bed and came to a conclusion that she would be pretty good. While she may be older that him and had been around the track a few times, that didn’t bother him. He thought that she was as some would say ‘experienced’, which would more than compensate for the age difference. Maybe she was a ‘cougar’ and if so it would be nice to find that out. He thought he would ask her out to see if she was interested in him.

As they were walking out the restaurant to their cars, Kevin said, “I really enjoyed the dinner and your company. I hope you don’t think I am being presumptuous but would you like to go out to dinner with me next week?”

He could see that his request again caught her off guard and she was thinking about what to say.

“You do know that I am older than you.”

“Oh, are you? I didn’t ask you what your age is, I asked if you wanted to go out to dinner. Your age doesn’t take away from the fact that you are an attractive and desirable woman and I enjoy your company.”

That response now caused her to blush and slightly stammer.

“I... , I... , I don’t know what to say, you have got me a little flustered by your invitation.”

“All you have to do is say yes.”

With a little hesitation, she said “Yes.”

She gave Kevin her business card which contained her private phone number for him to phone her to discuss the details.

Kevin opened her car door for her and watched her enter. Her skirt slid up a little on her nylon encased thighs and he thought that they were very nice.

He phoned her at work during the week to firm up the date. She expressed her concern of the age difference between them again and wondered why he would want to take her out to dinner.

Having confirmed the dinner particulars already Kevin finished the conversation by saying, “When you put the phone down, I want to go to the women’s restroom and look in the mirror. When you do, I want you to tell me what red-blooded male would not want to take you out, no matter what the age difference is.”

Pamela had no response to that comment and the conversation ended.

Kevin’s offer to speak on investing to retiring employees met with success. During the week a printing company and a large manufacturing firm accepted his offer to speak at their pre-retirement seminars. Two other corporations were seriously considering doing these pre-retirement seminars and said they would get back to him. While it would take some time to see if the soon-to-be retirees already spoken to and those he would speak to would want Kevin to be their financial advisor was something he didn’t know. He had some good vibes from the retirees who spoke with him after he gave his presentations.

With a little nervousness, he pressed the doorbell button on Pamela’s townhouse. He wondered a little about what the evening had in store for him. He had hopes that he would be successful in his pursuit of Pamela.

Some of his worry vanished when Pamela opened the door. She looked good in the light green colored dress she was wearing and he told her that she did. His telling her that brought a nice warm smile to her face. It seemed to him that some of the nervousness she had in going out with him had vanished.

Dinner was very nice mainly because of his dining companion thought Kevin. The dress she was wearing showed that Pam was not shortchanged in the breast department. They were more than ample in his opinion. He enjoyed being with her and he told her that he did.

When they arrived back at her townhouse, she asked him with what he perceived to be a little hesitancy in her voice, if he wanted to come in. He accepted her invitation which again brought a smile to her face.

Once inside, she asked him if he wanted something to drink. He walked right up to her and put his hands on her waist.

With his eyes boring into her eyes he said, “Instead of a drink, I was hoping I could have a kiss.”

Pam just looked at Kevin and didn’t respond, but she didn’t pull away from him either. He slowly bent to kiss her and she was looking at him as his lips descended to hers. He starting kissing her and she just stood there not moving or responding. After about ten seconds it was like a switch had been thrown, because she responded by wrapping her arms around him with her mouth opening and her tongue probing. His arms where around her and were moving up and down her back, stopping every so often to give her buttocks a squeeze.

He didn’t know how long the kissing went on but it was for a considerable amount of time. She finally broke the kiss and pressed the side of her head against his shoulder.

Kevin heard her quietly say, “The zipper of this dress is on my back,” and then she went right back to kissing him. He knew he had just been given the green light.

He was kissing her as he pulled the zipper of her dress down. He could hear her making little moaning sounds in her throat. When the zipper was down, she dropped her arms which caused the dress to fall to her hips. His hands went to her back where he unhooked her bra.

He said, “Maybe we should go where we can be more comfortable.”

She understood what he wanted and started walking to her bedroom, but she was still holding her unclasped bra against her breasts.

In her bedroom, he asked her to stop and turn toward him, which she did. He walked up to her and took her hands, placing them at her sides which caused the bra to fall away from her breasts.

“They stood higher when I was younger.”

“Well, they may not be the breasts of a young woman, but they are the womanly breasts of a very attractive and desirable lady. I think they are perfect.”

He put a hand under one of her breasts and raised it as he was bending to suckle on a nipple. She put her hands on the back of his head, pressing it to her breasts. His tongue flicking at her nipple was giving her some delicious sensations.

He raised his head from her breast and looking at her said, “Now will you please remove the rest of your clothing while I remove mine? I want to make love to the lovely lady that I see standing before me.”

That remark seemed to erase any further doubts she had about having a relationship with Kevin. She stepped out of her dress and took her panties off. She was lying on the bed with her arms extended to him, as he approached her. Instead of moving into her arms, he bent down and kissed her womanly essence which had a considerable amount of pubic hair. Him doing that elicited an “Oh, that is good” from her and caused her to spread her thighs further apart.

He vigorously worshiped her which he could tell she enjoyed because of what she was saying and how her body was turning and twisting. He knew she had some climaxes and a big one when he inserted two fingers to touch her G spot while nibbling on her clit. She gave one loud long moan as this happened.

Kevin moved up between her spread thighs. Showing her experience, her hand which she had wet with her saliva grasped his shaft and gave it a few strokes to lubricate it. She lined it up with her entrance and moaned as he slowly pushed his erect shaft tool into her wet warmth. Her heels rested on his buttocks as she moved her hips to hasten his full entrance into her.

The reluctance she had shown earlier had now vanished, because she said, “Give it to me Kevin and give it to me hard and deep.”

Kevin attempted to do what she wanted and based on her reactions, he thought that he was successful. His warm discharge into her caused her to have an orgasm and grip him tightly with her arms and legs.

Not wanting to have his weight rest on her, he rolled over with her now on top, still managing to stay coupled to her.

She nibbled on his ear and said, “That was wonderful, you are a good lover.”

“You were made to be loved.”

With her lying atop him both of them were quiet, each lost in their own thoughts. His hands were lightly caressing her backside, giving her fine globes a few squeezes. This caused his tool to start to harden and he felt her internal muscles lightly squeezing his tool at the same time.

She broke the silence when she said, “I know there was something I liked about younger men. They just can’t seem to get enough and are quick to recover. Do me Lover, do me again.”

Pamela’s lips and tongue concentrated on Kevin’s neck and ears, while her hips were going up and down. He had moved his palms to where they were under her breasts, with his thumbs flicking her stiff nipples. She varied the speed and motion of her hips, which further confirmed she was not a novice in the ways of making love.

He discharged into her warmth again. She gave him one long aggressive kiss before she decoupled and lay alongside him. Both of them told the other how good they were and how nice it felt to make love. She asked him to spend the night which he did.

He made love to her again when she awoke in the morning but this time it was slow and prolonged. Her arms were around him and she nibbled lightly on his ear. He knew she had an orgasm before he had his because she told him she did.

Although there was some reluctance on her part, they did shower together. Pamela offered to make breakfast but Kevin only wanted some coffee.

She was wearing a shiny silk robe as she sat at the table having coffee with him. Pamela thanked him for a wonderful evening. She blushed when she also thanked him she said, “For the other things.”

He said, “You know I hope this isn’t a one-time thing. If you don’t have any plans, I would like to take you out next Saturday.”

Smiling as she looked at him she replied, “I will save that day and the night for you.”

He gave her on last kiss at her front door and there was some passion in it that made it turn it into something more. While still kissing her, he opened her robe and pushed it off her shoulders. She lowered her arms, which let the robe fall to the floor. He bent and nibbled on her breast, while fingering her to an orgasm at the same time. She clung to him and after she climaxed told him that was one hell of a way to say goodbye.

He had some thoughts and nice memories on the drive back home. If she was correct when she said her body was better when she was younger, it must have been gangbusters back then. Her lovemaking skills were excellent. If this lovemaking was what he could expect from older women, he thought that he would be foolish not to seek them out for companionship. He couldn’t be sure if Pamela was representative of how older women acted with their dates, but if they were like her it seemed that you didn’t need to have three dates before they let you take them to bed.

Kevin made a mental note that he should try and confirm that thought.

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Story tagged with:
Ma/Fa / Consensual /