To Retire or Not
Chapter 5

Copyright© 2013 by Westside24

Erotica Sex Story: Chapter 5 - A man in deciding if he wants to retire completely gets involved in some interesting situations.

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

Although Lori had taken the edge off of Craig’s wanting female companionship, he couldn’t wait to see Monica who was flying down to Florida on Saturday. There was more to being with her than just making love. She was an intelligent lady and a pleasure to be with. She had a way of making him feel good when he was in her company.

He saw her coming down the escalator to the baggage claim area at Tampa International which put a smile on his face that wouldn’t quit. She also smiled and waved when she saw him waiting for her. They shared a kiss that caused them to get a few looks from the other people in the area. They were in his car on the interstate heading for Sarasota as soon as her two pieces of luggage were claimed.

They both expressed that they had missed each other. Monica said that based on the warm weather here she could see why Craig had chosen to winter down south. She asked questions about tomorrow’s cruise which she said was going to be her first time on a cruise.

“The two ports we’re going to visit are what some people call tourist traps and are similar to each other. The stores at these ports basically offer the same items for purchase. The cruise itself with the food and entertainment should be good. Some of the people I play golf with have been on this cruise and said it was something worth doing. I’m glad you’ll be going with me.”

Craig drove past his condo and out to Longboat Key. He stopped at a restaurant next to the water. Monica said that she was starved and seemed to enjoy looking at the younger people who were there having a good time. She told Craig that she could picture her daughter Kelly being among the young people.

Monica was impressed by Craig’s condo. She stood on the balcony gazing out at the nice view it afforded and told Craig that she could easily get used to this lifestyle. He took her in his arms and gave her a kiss. The intensity of the kiss increased and they soon were in the bedroom both naked on the bed making love. It was as good as he hoped it would be.

When they both had cum and were resting in each other’s arms, Monica looked at Craig and smiling asked him if this was a ‘nooner?’

He told her that it was and if she played her cards right, he would give her a ‘nighter’ later which caused her to laugh.

She did play her cards right because he gave her ‘a nighter’ after dinner back at the condo. He could have given her another one but he want to make sure he was saving himself for the cruise.

They drove over to the cruise terminal in Tampa the next day and they boarded the cruise ship after long-term parking the car. The boarding process was a little long because of the number of early boarders but it was trouble free. They familiarized themselves with the ship by walking around the various decks once on board. They stopped and had a drink at the Lido bar wishing each other a good cruise.

Craig thought it was a great cruise, not because of the ship but because he was with Monica twenty four hours a day. They made love every night and they also had two ‘nooners’.

One of the ‘nooners’ was with Monica bending over leaning on the desk in their cabin. They had taken a shower together which was a challenge in itself because of the shower’s size. She was bending over the desk looking at something after drying off when he came up behind her. She started wiggling her hips when she felt him against her butt. That’s all it took for him to put some pressure on her to bend her forward more and he thrust his shaft into her moist sheath. They both were looking at the expressions on each other’s face in the mirror while they were making love which heightened the excitement.

Monica’s outgoing personality encouraged Craig to participate with her in a number of activities offered on board the ship. Dance lessons, two variations of trivia, and various lectures by the ship’s personnel were all on her agenda.

They didn’t take any of the offered tours when they were in port and were content to walk the shopping area, holding hands and visiting the numerous shops to see what was being offered for sale. Monica purchased a gift for Kelly.

As far as Craig was concerned the cruise ended all too soon. They shared one more night together at his condo and he drove her to the airport the next day as she had to get back to work. Saying they would stay in touch he gave her one last kiss before she walked past security to board the tram to her departure gate. Craig was sad at her leaving as he drove back to Sarasota.

With Monica now gone, Craig tried to brighten his mood with the various activities he participated in but it was difficult. He signed up to go out on party boat fishing to do something different. He caught a number of mangrove snappers before he had a good bite. He landed a twelve pound grouper after about a ten minute fight. This temporarily brightened his mood but it was short-lived when he was told the fish was out of season. The fish was released after a quick picture.

He seemed to be coming out of his funk and was now starting to not only miss Monica, but also miss female companionship. Craig remembered the lounge Lori had pointed out when they were going to the polo match and that she had said they had a band that played there on the weekends. He figured that he had nothing to lose since it was Friday. He headed off after washing up and dressing to see if there was any ‘talent’ there.

He thought there would be a good crowd in the lounge based on the number of cars in the parking lot. He was right, there was a good crowd in the lounge and by the noise they all seemed to be having a good time. He was able to find a seat at the bar and ordered a drink. He carefully eyed the other patrons. He was pleased to see that it was an older crowd with some of the people older than him but on average the majority were a few years younger than him. It seemed like it was two men to one woman, which was a surprising good ratio. A number of the women were attractive from what he could see. The band was playing older, slow tempo songs and there were about ten couples on the dance floor.

Craig was on his second drink watching the interplay between some men and women when he felt a tapping on his shoulder. He turned to look to see who was doing the tapping and saw a nicely dressed lady standing there.

“I was wondering if you would care to dance.”

“It will be my pleasure if you want to take a chance of me not stepping on your toes.”

He followed her out to the dance floor and came to two conclusions. The first one was that she had a nice butt in the tight dress she was wearing and the second was that she was close to his height in her high-heeled shoes. This was a tall lady.

They introduced themselves on the dance floor. She said her name was Laura Perkins and that she was a full time resident of Sarasota. The small talk ended when he completed his introduction and she moved in against him as they danced cheek to cheek. Besides her cheek touching his, her breasts were pressing against his chest. Craig’s hand was a little low on her waist just at the top of her buttocks, but she didn’t say anything. They danced four slow dances before she said they should take a break.

He asked her if he could buy her a drink and she accepted his offer. She asked him to join her and her friend at the table they had. She introduced him to Judy who was sitting at the table saying that Judy was a good friend. Judy was a blond-headed lady who was showing a lot of cleavage. Both Judy and Laura started asking Craig questions about himself and he gave them truthful answers about his situation and why he was in Florida.

Craig asked questions of these two ladies and while they answered it seemed to him they were holding something back. Judy was asked to dance by some fellow that caused her to leave the table. Craig asked Laura if she wanted to dance some more but she replied that she would just as soon just sit at the table and talk to him if he didn’t mind. That was fine with him since he enjoyed her company and she seemed to be an intelligent woman.

Judy came back to the table after some time had passed and told Laura they should be leaving in ten minutes. Laura said that she needed to go with Judy since she had ridden here with her.

Craig now had to make a decision as to whether or not he should volunteer to give Laura a lift home instead. Something was telling him he shouldn’t offer Laura a ride home. He thought that she would think he was just looking to get her in bed if he did. That thought did cross his mind but he knew that first had to do a little courting with most women before that would happen.

“I’m sorry to see you’re leaving. I really enjoyed talking to you tonight. If it doesn’t present a problem I would like to take you out to dinner sometime. Please don’t worry about saying no to my offer if your acceptance does present a problem. It was very nice meeting you either way.”

It seemed to him that Laura wasn’t expecting him to ask her out and she seemed a little stunned that he did.

After a short time she said, “I don’t know what to say. Most men would have volunteered to drive me home instead of Judy not that I would have accepted their offer. You’re a little different in that you didn’t make that offer. I did enjoy talking to you and yes, I would like to go out to dinner with you. Here is my card with my contact information. Call me when you want to go out to dinner.”

“I don’t need to call. Are you free for dinner tomorrow?”

Laughingly she said, “You’re a fast worker and there is no grass growing under your feet. Okay, you have my address and can come to my place at six.” She stood up to leave with Judy. Laura gave Craig a kiss on his cheek before she left.

When he was preparing for his date with Laura he wondered how it would turn out. She wasn’t out and out beautiful but she was attractive and there was something intriguing about her. He thought it would either be an interesting or a bummer of a night. There was something about Laura that had Craig thinking. It just wasn’t her looks which were nice, but there was something. He just couldn’t put his finger on what it was.

Craig made a reservation at a nice French restaurant that was close to the water. Maybe he was going overboard with the restaurant choice but something told him it was the right thing to do.

Finding Laura’s residence with his GPS wasn’t a problem. It turned out that she lived in a tall and seemingly affluent condominium building, just off Bayfront drive. He pressed the button next to her name at the building’s entrance. He heard a buzzer which enabled him to open the door. He took the elevator to the top floor. Since it was the top floor Craig thought that she must be living in a penthouse condo.

Laura was standing at her open door and waved to Craig when he left the elevator. He walked up to her and admiring her in the dress she was wearing he gave her a little wolf whistle which caused her to smile and blush. He could see that the dark red dress she was wearing didn’t come off the rack at Kmart. He would also guess that the large diamond stud earrings she had on were real and not fake.

He walked into her condo and was impressed by what he saw.

“Do you want a cocktail before we go?”

“Only if you’ll join me.”

Craig had the opportunity to look at the condo’s decorations and furnishings while Laura was making the drinks. It only said one thing to him, ‘MONEY’.

As Laura handed Craig his drink he thanked her for the drink and complimented her on her nice condo.

In taking a seat Craig said, “We can’t dilly dally here too long, because we will miss the early bird special at the Shrimp Shack if we do. They have a five dollar all you can eat special tonight.”

He could see that his remark stunned Laura. She didn’t know what to say as she hadn’t dressed up like this to go to the Shrimp Shack.

Craig finally said, “I’m only kidding, we’re not going to the Shrimp Shack. I’m only teasing you. I made a reservation at ‘Chez Jean’.”

She laughingly said, “You almost had me there, I will need to watch myself with you. Your teasing had me going and I believed you.”

His teasing her seemed to break the ice and maybe took away some of the apprehension Laura had of Craig since she didn’t know him very well.

They drove to the restaurant where Craig had his car valet parked. The Maitre d’ warmly greeted Laura by her name when they entered the restaurant. This started to make Craig wonder what he was getting himself involved in with Laura.

They placed a drink order and took some time to get to know each other at their table. The questions Laura asked Craig resulted in him giving her the history on himself and why he picked Sarasota to spend his winters in.

 
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