To Retire or Not
Chapter 1

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

Desc: Sex Story: Chapter 1 - A man in deciding if he wants to retire completely gets involved in some interesting situations.

Being out of work gave mixed emotions to Craig Jacobs. The bank that Craig worked for had been bought by a larger bank and they didn’t need two heads of the mortgage department. Craig was offered a lesser position but it was at the larger bank’s headquarters which was just outside of Detroit, MI. If he wanted this position he had to leave his Naperville, IL condominium and relocate to Michigan. The decision was a no-brainer as far as he was concerned. He turned the job offer down and accepted the buyout package that was offered.

Craig had started work at the bank right after graduating from college. His Aunt Ruth, his mother’s older sister was married to the bank president. Besides listing her as a reference on his application for employment he suspected that she made a phone call to the bank which assured they would make him an employment offer.

Craig had rapidly progressed to where he was made head of the mortgage department in only two years. While he was young for that position and his promotion generated some comments about nepotism, he was able to display that he was an effective manager in a short time. There were a number of things that he did in his career that reflected his strong management ability. If he had to pick one thing he thought was the highlight of his career, it would be not giving in to the pressure the Federal Government exerted to approve mortgages to unqualified applicants. He did however approve some mortgages where the applicants could only put ten percent down on the home they were purchasing. He did that only because the applicants showed that they could generate sufficient income to handle the monthly payments.

Craig’s Aunt Ruth who was a widow had passed away three years ago. She didn’t have any children and while she did make some small charitable bequests, the bulk of her estate was willed to Craig. She was his godmother and the son she never had. The shares of stock in the bank she willed to Craig made him the bank’s largest individual stockholder but he didn’t exercise the power that those shares gave him. Couple that with the shares he had accumulated through exercising stock options and purchasing other shares with his bonus money made him a wealthy individual. This wealth further increased when the buyout offer by the large bank became known which caused the share price of the stock to almost double.

He was content to be the head of the mortgage department and was not interested in being the bank’s president. To him it was a turn off to have the headaches and play the politics that came with that position. Craig had also voted in favor of the buyout because of the rise in the share price which benefited all the shareholders and not just him. His yes vote effectively put him out of a job. Deciding what he wanted to do now that he didn’t have a job had been on his mind for the past two weeks.

The economy was in such bad shape that most banks were reducing instead of increasing staff. He could probably find employment but it wouldn’t be anywhere near what he had enjoyed doing which made that avenue unappealing and something he wouldn’t do. Travel or relocating to a warmer climate were two things he was considering but he hadn’t yet decided on what to do. He did know that his winters wouldn’t be spent in Naperville, IL, but whether they were going to be spent in Arizona or Florida was something he hadn’t yet decided on.

Craig was single and probably a confirmed bachelor at this stage in his life. At fifty three years of age he hadn’t yet found a woman he wanted to marry and was starting to doubt that he ever would. He was fairly good looking with a six foot-two inch frame carrying his two hundred pounds. Normally he didn’t have much of a problem in finding women to date. Should the woman Craig was dating start to talk or give hints that the arrangement or relationship he had with her should become permanent, because he didn’t have serious feelings for her this was an instant turnoff for him. While Craig didn’t immediately stop dating these women, he reduced the frequency of the dates until he no longer dated them.

After finishing his second cup of coffee this morning, Craig thought it was time to do some chores. He would normally do his laundry after he came home from work or on a Saturday or Sunday but he could now do it on a weekday and the first thing in the morning. He gathered the items he wanted to wash and walked down the hall to the laundry room.

He saw that it was already occupied when he opened the door and he was looking at the very nice backside encased in tight slacks of his across the hall neighbor Lori. She was standing by the washing machine.

“Excuse me, I didn’t know the room was occupied. I’ll come back later.”

“No reason for you to leave. I’m done with the washer and the items I’m putting in the dryer will be done about the same time as your wash.”

Craig thanked her, loaded up and started the washing machine. He then went back to his unit.

He had another cup of coffee and thought about Lori. Craig had only been living in this condo for about a year. He had never spoken to Lori in depth, just saying “Hello” or “Good evening” when he saw her. That isn’t to say he didn’t know anything about her. He guessed she was around his age, somewhere around five foot-seven inches tall, and about one hundred and thirty five pounds or so. Besides having a nice backside, her strongest physical assets and there were two of them, were her breasts. They had to be thirty eight double D’s.

Stan Huntley was Craig’s next door neighbor. He knew everything about everybody in their building. Stan said that Lori was married to John, her third husband who was considerably older than her. According to Stan, Lori had a few live-in boyfriends she before married John. It was said that Lori liked and wanted male companionship. Stan further related that Lori has been married to John for about a year and half. John had a heart attack which resulted in bypass surgery six months after they were married. He seemed to have recovered well from the surgery.

Craig was aware that Lori was an attractive woman and per Stan spent her winters in Florida. He thought that she could be a good source of information about the pros and cons of wintering in Florida.

He heard Lori’s door close and looking at his watch saw that it was a half hour since he started the washer. With that time passing he thought his wash should be done.

He saw Lori bent over, taking items out of the dryer when he entered the laundry room. ‘She has a nice ass’ was the thought that ran through his mind. She turned and smiled at him.

Craig asked her how John was doing as he was taking items out of the washer.

“He’s doing well for the most part. He’s back in Boston right now overseeing some repairs to an apartment building he owns that was damaged by a small fire. He is going to list the building for sale once the repairs are done. He’s due to come back here Saturday evening.”

“What do you do when he is away?”

“I have some girlfriends in other buildings who take up my time during the day but the evenings are a little boring. There isn’t much on television that I care to watch in the evening.”

“I couldn’t agree with you more. I find the evenings to be a little boring as well. I was wondering off the top of my head if you might like to go out to dinner with me this evening. Someone told me that you spend your winters in Florida and that’s something I am considering doing. Dinner would give me the opportunity to pick your brain and ask you questions about wintering there. I am debating between Florida and Arizona, and haven’t decided where I want to winter at.

“Sure, there are two more days before John gets back, so why not.”

“Is six o’clock okay?”

“Fine with me.”

Back in his condo, Craig wasn’t sure what possessed him to ask Lori to go out to dinner but she was an attractive lady. He thought that besides getting her take on Florida he would also be getting to know her which should be interesting. She could have refused his invitation since she was married but she didn’t which gave him more to wonder about.

He pressed her doorbell button at six sharp and she opened the door ready to go. There was no one in the hallway to see them as they walked to the elevator. He thought she looked good in the high heels, tan slacks, and the green satin blouse she was wearing. She did have a sweater over her shoulders in case the temperature in the restaurant was too cool.

They entered the elevator and pressed the down button. The elevator made one stop at the next floor and Marie Collins walked in. Marie was the Condominium Board’s Secretary. Just like Stan, Marie knew everything about everybody.

Craig smiled and nodded at Marie.

Marie’s attention was on Lori however because she asked her, “Going out?”

Lori was a quick thinker as she responded, “Yes, Bill and Hillary Nixon who live in Burr Ridge have invited me to go out to dinner with them. I think they want to show me pictures of the recent cruise they took through the Panama Canal. Where are you going?”

“It’s duplicate bridge night at the clubhouse and I’m in charge of this week’s session. I need to get the room and tables ready.”

All three of them exited the elevator when it stopped at the first floor. Marie and Lori continued to talk while Craig left the building. Without Marie seeing him he signaled Lori the direction in the parking lot he was heading.

Craig was sitting in his car for five minutes before he saw Lori heading in his direction. He exited the vehicle in order for her to see where he was.

Once she was in his car Lori said, “That Marie is a nice lady but she just wants to talk and talk. If she knew you were taking me out to dinner everyone in the building would know about it in a short time. There’s nothing wrong in us going out to dinner but I just as soon keep it to ourselves.”

“I thought the names of Bill and Hillary Nixon went over well. You were pretty slick with that response”

“Those were the first names that came to mind.”

“You could have said George and Barbara, or George and Laura, but I think you would have gone over the line with Barack and Michelle, or Ike and Mamie.”

Lori just laughed at his comment. She had a pleasant laugh.

Craig drove over to a restaurant that was located in the next suburb. It should be far enough away from the condo and its residents for them to dine unnoticed.

Dinner with Lori was quite nice. Besides her good looks she was quite knowledgeable on a number of topics. Maybe it was the two martinis she had before their meal that loosened her tongue, but Craig enjoyed hearing her talk.

He asked her about her life which she responded, “Well let’s see, I was born and raised in the area here. I did go to Texas for college where I met Richard my first husband. We were married right after graduation and both of us went to work for a startup computer company in Austin. Dick was into computer leasing and I was with inside sales. Things were tough for this company and they couldn’t meet the full payroll at times. They compensated by giving us generous stock options instead of our full paycheck. Dick and I believed in the company’s future and it turned out that we were right. The company took off and the shares we had doubled, then tripled, and split three times. We knew better than to keep all our eggs in one basket as they say, so we sold most our shares to diversify. While we didn’t sell at the top, we were close to it.”

“That was the good news. The bad news was that I came home one evening and found Dick slumped on the floor. We had been married for sixteen years. An ambulance took him to the hospital where he was diagnosed as having an inner-cranial aneurysm. There was nothing that could be done and he passed away two days later. Now that Dick was gone I moved back here to be closer to my parents.”

“I met Ray Barnes at a high school reunion a few years later. He was our class president and had become a very successful lawyer specializing in class action lawsuits. We started dating and one thing led to another and he asked me to marry him which I accepted. Besides being a successful lawyer, he was very good in making real estate investments. As an example, he bought some farm land that the State later wanted when they were extending their toll road system.”

“He became aware of a new condominium that was going to be built in Sarasota, Florida. He put money down on four units before the first shovel of dirt was turned. He sold two of the units for a nice profit just before the occupancy permits were issued. He rented one of the remaining units out and wintered in the other. He sold the rental unit for a considerable profit four years later and used that money to pay off the mortgage on his unit. After everything was said and done, the unit that we wintered in cost him practically nothing and has greatly appreciated in value. That’s where I presently winter. The pressure of the court room unfortunately took its toll and Ray died from a massive heart attack.”

“After Ray’s death and while down in Florida, I met John who was a resident and a widower in my building. John is a retired veterinarian from the Boston area. We started dating and he asked me to marry him. He treated me quite well, so I accepted his proposal. We have been married about a year and a half now.”

“Any kids?”

“The only children from any of my three marriages are John’s. He has a son and a daughter both of whom are doctors.”

“How do you get along with them?”

“Funny you should ask, the relationship I have with them it is rather cool. I know I will not replace their mother and while they seem to be happy that John has remarried, I get the impression they think I am something of a gold-digger. They don’t know that I am considerably wealthier than John but I haven’t told them that. As far as I am concerned that isn’t any of their business. Now all this talk has been about me, please tell me about you.”

Craig told her about his life, the bank, the merger, his early buyout and now his turmoil on deciding what he wanted to do.

He could see that Lori was interested but curious when he mentioned that he was single and had never been married.

He thought he should immediately eliminate any possible concern she may have and said, “That I’m not nor have I ever been married doesn’t mean I don’t like women. I do, believe me I do. It just that I haven’t found the right woman and I may never will but that doesn’t mean I’m not looking. Let me unequivocally say that I like women and all that they are and I only want men as friends, not as lovers.”

That remark caused Lori to giggle and maybe to become slightly relieved that Craig confirmed his preference for women.

This was a very nice evening but the meal was over all too soon and it was time to head back to the condo.

Craig asked Lori to tell him about Sarasota on the drive back. She talked about the weather and the many activities that were there, such as theater, golf, polo, fishing, the beach, and a number of other activities that were available to do there.

Craig was also thinking about her while listening to her. There was no question that she had a nice figure and a prominent rack. Based on what she said about her life he thought she was maybe a few years older than him, but you couldn’t tell that by looking at her. She looked younger than him. Her face didn’t have a wrinkle on it. She either had great makeup or had a face lift. She was one good looking woman and he wondered how she would be in bed. He thought and would bet that she would be a tigress in bed.

They shouldn’t run into any residents at the condo at that time of the night in going back to their condos and they didn’t. Lori said she had a very enjoyable time as they walked to their units and surprised him when she asked Craig if he wanted to come in for an after dinner drink. He said he did.

Craig sat on the couch while Lori poured two Kailua and creams on the rocks. She took a seat on the couch next to Craig and they continued to make small talk, mainly about Florida.

They placed the empty glasses on the coffee table when the drinks were done.

Lori turned on the coach toward Craig and placing a hand on his thigh said, “You asked earlier about how John was doing after his procedure and I said generally fine. What I didn’t say was that whether it’s his heart or the medicine he’s taking, but he hasn’t been able to achieve an erection ever since the procedure. In addition, he doesn’t believe in giving head although he likes it when I do. He bought me a vibrating dildo and while that helps get me off, it’s not as good as the real thing.”

Craig was somewhat shocked to hear her say what she just said. Maybe it was the alcohol talking. He could tell that she was waiting for some response from him. Her hand on his thigh was like a little electric shock. It was a lot of information she had given him. He thought that contained in this information overload was that he was being given a green light by her. Craig turned toward her and put one arm on the back of the couch.

Looking into her eyes he could see the passion that was there. He slowly moved his lips toward her lips and saw that she wasn’t moving away.

Her mouth opened when his lips touched hers and her tongue immediately started searching for his. Lori’s arms went around him and his arms went around her. He doubted that there were any limits placed on him and he knew where this was heading. He confirmed this when his hand cupped her large breast and heard her moan. He started to unbutton her blouse and she let him.

Once the blouse was unbuttoned, he reached behind her and unclasped her bra. Going under her unloosened bra, he cupped her large warm breast and felt her rigid nipple press into his palm. He was a little surprised by the firmness that he felt in this breast. It was firmer than he expected it would be.

The kissing went on until Lori suggested that they should go to the bedroom where they would be more comfortable.

He followed her into the bedroom and watched her undress as he himself was undressing. She was done first and she turned and waited for him. Based on the shape of her breasts, Craig thought that somewhere along the line she had some implants put in. He saw that there was no pubic hair when he looked at her most private part and he expected that there wouldn’t be any for some unknown reason. She had an hourglass figure with large breasts that tapered into a narrow waist and flared out to womanly hips. The high heels she was wearing highlighted her long slim legs. It wasn’t the body of a twenty year old but it was one hell of a body.

He stood and went to her when he was undressed. She still had her high heeled shoes on and welcomed him into her arms. They resumed kissing, but she had a way of rubbing her naked body against his while they were doing that which further excited him.

He motioned for her to lie down on the bed and she did so. He moved to join her, and maybe surprised her a little when his face moved in between her thighs to pay homage to her most private part. This was something she must have been hoping for because she started twisting and became somewhat verbal.

“Oh my God... , that is so good so good... , I love it and what you are doing... , that’s the spot... , don’t stop... , Oh my God, I am cumming... , don’t stop.”

He didn’t stop as she climaxed. He had enjoyed giving her head and seeing her reaction.

He didn’t know how many orgasms Lori had but she had a number of them. She finally asked Craig to stop because she said she couldn’t take anymore. He moved up and laid alongside her giving her another kiss in which she tasted her juices on his lips.

“That was good. You certainly know what you’re doing. How about if I do some payback?”

“Maybe later because you have me so excited that I will cum right away if you do that.”

“No you won’t” and she flicked her finger, giving a snap to the head of his rigid shaft.

This was surprising and it seemed to cool his excitement a little. She put a thigh over his hips and mounted him reaching down to insert his rigid shaft into her. His shaft was telling him of the warmth that was within her. She slowly moved her hips and he was content to let her set the pace. Her breasts were hanging down to where he could suckle on the nipples. He alternated suckling on each breast and was content to watch the emotions that her face displayed as her hips were moving up and down.

He lasted longer than he thought he would but eventually he was spewing his warm spend into her. She smiled when she felt this warmth and just collapsed on him. They were still coupled together and she was telling him how good of a lover he was.

Lori wasn’t done for the night, but she knew Craig needed some time rest to recharge his batteries. She asked if he was uncomfortable with her lying on him. He told her to stay where she was. There was a little talk between them, but each of them had their own thoughts about what had just happen.

She started to squeeze her muscles that were toned by the Kegel exercises she did. With her probing his ears with her tongue he could feel his shaft that was in her reacting to her doing this. She knew what she was doing because he again was in a state of readiness in a short time. He surprised her when he twisted around so that she was on the bottom and he was on top. His shaft was going deeply into her. His arms where underneath her legs and elevated them which enabled him to raise her knees and hips so that he could get the deepest penetration. Her feet were pointing to the ceiling. Her arms were around him bringing his face next to hers so she could kiss him and nibble on his ears.

To say she was experienced in the ways of making love would be an understatement. Her hands were touching him in spots that he never knew were sensitive. His warm spend into her again caused her to have another orgasm.

Both of them rested and did a little more kissing, but they eventually fell asleep in each other’s arms.

He wasn’t sure who awoke first, maybe they both did at the same time.

She raised her head a little and smiling at him, said, “It wasn’t a dream, you really know what you are doing. I am sore down there and it has been a while since I could say that.”

“You are no shrinking violet yourself and you certainly satisfied me.”

Her hand drifted down his torso and found his morning woodie had him in a state of readiness. Without any further preliminaries she put a leg over his hip and reached down to insert his erect shaft into her. Nothing was said as his shaft was plunging into her because of her hip movements. Each of them just stared into the other’s eyes, intent on seeing the other’s reaction. In a way it was a challenge to see who could give the other the most pleasure. His moisten thumb rubbing her clit raised the stakes. Craig thought it was intoxicating to make love this way in the light of the morning. Their mutual orgasms signaled they had each accomplished their mission.

Lori offered to make breakfast and Craig accepted her offer. Sitting at the kitchen table having a cup of coffee he enjoyed the sight of Lori wearing a short and somewhat transparent chemise while she was preparing breakfast. She was a good cook and the ham and scrambled eggs hit the spot.

Craig caught her arm as she was picking the dishes up and had her sit in his lap. He gave her a kiss that she eagerly accepted.

Looking into her eyes he said, “I was wondering if I could ask you a serious question about something that deeply concerns me?”

Wondering and maybe a little worried where he was going with this she said, “Yes you may, what’s the question and what has you so concerned?”

“Well... , well... , I know John is coming home tomorrow night, but I was wondering if you would like to go to dinner with me tonight.”

His statement brought a smile to her face as she replied, “You can bet your bottom dollar that I will. I was hoping you would ask me but I would have asked you in case you didn’t. You know how to show a girl a real good time. I was thinking that instead of us being seen walking out together and maybe meeting Marie again, how about if I just meet you down at your car at six thirty? The tongues in this building won’t start wagging as we won’t be seen leaving together.”

With a look on her face that was sort of impish she said. “I might suggest you get some rest as you’re going to need it.”

She moved to give him one last kiss before she checked the hallway to make sure no one was there to see Craig leaving her condo to go across the hall to his.

Back in his condo Craig couldn’t help but think that Lori was right on about him needing the rest. He took a three hour nap. He lay in bed for a while when he awoke and thought about Lori. She certainly was all-woman and maybe more woman than he could handle. He chuckled to himself as he thought that she enjoyed and knew how to make love. He thought that she was the most experienced woman he had ever made love to. This coming evening should be one exciting evening. He was going to be sure to take a Cialis pill before he left his condo.

He left his condo a few minutes before six thirty and purposely closed his door hard to make enough noise so that Lori would know he was leaving.

He was in his car waiting for Lori and he saw her walking to his car shortly thereafter. She looked good in the high heels, dark red dress that showed some cleavage and she was wearing her hair up. There was a subtle sway to her hips as she walked to the car.

When she was seated, Craig said, “You look absolutely delicious.”

“Good enough to eat?”

That remark caught him a little by surprise but he looked intently into her eyes saying, “That’s for sure.”

His response put a smile on her face and caused her to blush. He wondered if she moistened hearing his response.

Craig thought that the foreplay already had started as he drove to the restaurant.

The two drinks each of them had before the meal was served did loosen their tongues a little. While the meal was good, the sexual innuendos exchanged in the conversation only heightened the interest in what both of them were expecting to happen later. They were seated in a booth and Lori played a little footsie with Craig. He retaliated by putting his hand on her inner thigh under the table and stroked it a little which increased the lust he saw in her eyes.

They walked into her condo when they got back at the building. She put her purse down, and turning, she put both of her arms over Craig’s shoulders and brought him to her for a smoldering open-mouthed kiss.

She leaned back in his arms when the kiss ended and looking at him said, “I have wanted to do that all evening. Do you want something to drink or do you want something else?”

His response was just to bring her back to him for another kiss. He reached behind her and pulled down the zipper on the back of her dress while he was kissing her. That being done, he reached in and unfastened her bra.

She knew what he had done because she leaned back and said, “I can see you want the something else” and turned to walk to her bedroom.

He followed her to her bedroom, watching her step out of her dress, discard the loosened bra, and shimmy out of her panties. She then stood and watched Craig as he undressed.

He came to her when he was naked and kissed her while he enjoyed the way she rubbed her naked body against his.

The kissed ended and he motioned that she should recline on the bed.

She did, and he said, “Remember what I said in the car?”

There was some wonderment expressed on her face trying to remember what he said but that instantly vanished when she saw him bend and his face went in between her spread thighs. His enjoyment of her was just like she hoped it would be. Lori lay back and thrilled to the sensations he was giving her. She didn’t want it to end but she wanted Craig to enjoy himself as well not that he wasn’t enjoying himself now. She asked him to twist around so she could taste him. He did and it didn’t take long after she mouthed him for him to give her a large discharge that caused her to gag a little.

They rested for a while but after some more kissing and fondling, they were at it again with her on top. Her nipples were grazing his lips which he would periodically capture and suckle on. He lasted longer this time but the inevitable happened and he gave her another load into her warm and wet sheath.

They rested again and he thought that was it for the night. Lori had other ideas and with her help, mainly her oral stimulation of his love shaft and possibly that of the Cialis that he had taken, he was able to satisfy her one more time before both of them fell into an exhausted sleep.

His woodie wasn’t quite as stiff has it was the morning before when they awoke but with Lori’s oral help he was able to make love to her again.

At his suggestion they showered together. He enjoyed groping her slippery and soapy body and was able to finger her to an orgasm. Being with her was an unforgettable experience. The enjoyment she had in making love was evident.

As they were finishing breakfast Lori said, “Being with you was something that I really enjoyed.”

“Amen to that and that goes for me too.”

“John is coming home tonight and that will put an end to this affair I am having with you as long as he’s home. I don’t want to take a chance of him finding out and hurting him while he’s is here but if he goes out of town again that’s another story. I am sorry to say that there is nothing that I know coming up which will have him going out of town.”

“I agree with you. It’s only right that we don’t fool around with John in town. I will say that there will be some thoughts that I will have of how great these two nights have been whenever I see you.”

“Thanks, that’s very nice of you to say that and it’s also how I feel. I... , I don’t know what your situation is with having any current lady friends but I have a girl friend who lives one building over who I think could use ‘your services’. I could give her a call and set it up for you if you want. You may have seen her with me. She’s about my size and has flaming red hair. I will say that in my opinion she does have a nice body as well as being a nice person. I think you would enjoy going out with her in more ways than one.”

“You’re not going to tell her about us are you?”

“No, but I can hint around on what a stud you are. As I said, I think you would enjoy going out with her. I’ll bet she will enjoy going out with you. Between you and me, she hasn’t been laid in over a year.”

That last comment took Craig back a little.

“Let me give that some thought and get back to you if it’s something I want to do.”

It was one long last kiss that they had with Craig giving her butt a long and solid, two-handed grope before he left her condo to go to his across the hall.

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Story tagged with:
Ma/Fa / Consensual /