Wintering
Chapter 3

Copyright© 2015 by Westside24

Sex Story: Chapter 3 - A story about a man who decides to head south to avoid the cold weather and gets involved in interesting situations and meets some women.

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

Bill Meyers was back in his routine since he had come back California. His going to his two car dealerships to see if he needed to do anything and golfing were now the highpoints of his week. He still thought about Traci and what might have been but he had accepted that it never will be. While he had somewhat put the relationship he had with her behind him, there were the memories he had of her that would not be forgotten.

At work he continued his practice of periodically visiting all of the departments in his two dealerships and speaking to each employee individually. Bill would thank them for doing a good job and the contribution they were making to the success of the dealerships. He long ago had realized that managing of this business meant managing the employees as they were the faces of the dealership and contributed to its success. He emphasised with them the importance of treating the customers with respect, even those customers who at times were difficult to deal with.

While the business was going good his social life especially after Traci was on a big downer. His friends both male and female had offered to fix him up with women they thought he would enjoy dating but Bill was not a fan of these blind dates and politely passed on the offers that were made.

That changed a little one day after golf at the country club. Bill was sitting at a table with his three friends that he golfed with having a few beers and generally just shooting the breeze. He was talking to Cal Stevens when he noticed Cal’s wife Joanna, walk into the lounge accompanied by a very attractive lady. They both were carrying their tennis rackets which told him what they had been doing. The tennis outfits they were wearing emphasised their long slim legs.

Talking to Cal, Bill said, “Who is that fox with Joanna?”

Turning his head to see who was with his wife Cal turned back to Bill and said, “That’s Lynn, Joanna’s sister. She came here to visit for a while and seems to have gotten over her divorce. That’s who Joanna and I have been trying to fix you up with.”

“Well try harder.”

“If you are serious about that, wait till they come back from the locker room and we will join them for a drink and I will introduce you.”

“Sounds like a plan.”

Bill knew he was feeling a little buzz from the beer he was drinking, but that did not take away from the fact the Lynn was a very attractive lady. It would do him good to meet some new ladies and if Lynn was indicative of whom his friends were trying to set him up with, maybe he should have more of an open mind about their efforts.

When the two ladies came back and sat at a table, Cal and Bill walked over and joined them. Bill was introduced to Lynn and confirmed that she was indeed an attractive lady. She was of average height with dark brown hair, decent size breasts and a very cute face with bedroom eyes that just made him melt. He shook her extended soft hand probably too long and embarrassed himself a little.

While Cal and Joanna gave Lynn the particulars on Bill, he was able to learn a number of things about Lynn. She had been divorced for seven months and was a high school teacher where she lived in Clearwater, Florida. Lynn didn’t have any children and liked to spend the summers travelling and leaving the hot and humid weather of Florida.

Bill asked her about her travels and her favourite places to visit.

“Hawaii would be my number one choice with Italy a close second. Both places are nice and do cater to the vacationer but both are a little expensive.”

“Do you have any places or vacations you wouldn’t recommend?”

“Not really... , while I do like cruising and I just got back from one, taking a cruise in the summer is not high on my list of things to do. Besides the families with their children, it seems like all of the passengers are single female teachers like me who are off for the summer.”

There was more conversation about what Lynn was doing while she was visiting here as well as Bill being in Arizona and his dealerships. There was an agreement amongst the four of them that they would meet later back here at the club for dinner. The seafood buffet that they served here on Fridays was worth going to.

Back at his townhome Bill was having some thoughts about Lynn and the predominate one was what kind of a lover would she be? Was this wishful thinking on his part? It probably was but there was that old saying of “Hope springs eternal.”

Bill had always believed in setting goals and getting Lynn into bed was his newest goal. His thoughts were on how he was going to accomplish this.

Seeing Lynn walk into the lounge where Bill was having a drink along with Cal and Joanna, only confirmed to Bill that he had set the right goal. She was wearing a black sleeveless dress four inches above the knees that showed her to be a very attractive lady. As she walked up to him there was something in the sway of her hips that was eye catching.

Bill gave Lynn his bar stool to sit on and he ordered a round of drinks for all of them.

Later at the table they had another drink and then they visited the buffet. The meal and the conversations were good and spirited. Lynn had a definite liberal bent in her politics. Bill would have like to argue with her on what the present administration was doing and had screwed up, but that probably would have pissed her off. He didn’t need to argue with her because Cal took the lead on that and clearly was the winner if one was scoring this as a debate.

When the band started to play Bill asked Lynn if she wanted to dance. She said she did and he watched her pretty backside as she walked to the dance floor.

“I thought in asking you to dance would give you a time out from the debate you were having with Cal.”

“Oh, we always go at it. He is too far right for my tastes but he does take good care of Joanna. You were a little quiet there. I wonder whose views on what was discussed you preferred.”

“Lynn that question puts me in a no win situation.”

“Why, are your views as extreme as Cal?”

“Not quite but close to it. I don’t care for politicians who say one thing and two years later when they are elected to office say the complete opposite. Some of them have out and out lied about laws they propose just to be elected. We both have seen a politician deny knowing anything about embarrassments that occur during his administration and yet claims to know about everything when something positive happens. Your political party wants to decide what is best for all of us and feel we should pay more in taxes but refuses to cut spending. Voting to pass a bill that they never read which affects one sixth of this nation’s economy shows their incompetence. Couple that incompetence with the bullshit these career politicians say makes me a big supporter of term limits. For some reason people in government think those of us who aren’t in government are stupid. I think you can tell I hold an opposite opinion on that. Another sore point with me are the politicians who exempt themselves from laws they pass that we have to comply with.”

He could see she wasn’t a fan of what he said but she said, “Go on, I am sure there is more you want to say.”

“Well your party wants to redistribute the wealth and make people more dependent on bigger and bigger government. I think when one of your leading Senators said “We don’t represent our constituents; we represent our party,” he said it all.”

“So everything you party does is the right thing to do?”

“Far from it, we too have members that are loose as a goose when it comes to spending the money. We also have a Senator who never met a war he didn’t like. He wants to send our troops everywhere and have us be policeman to the world. I think we should bring our troops home, especially from Korea and Europe. Let those nations defend themselves as they can afford to.

With a very innocent look he said, “Now before you say anything since my views are different than yours, just remember that opposites do attract.”

Making that last remark to Lynn caused her to laugh.

He brought her closer to him as they danced. Lynn didn’t resist the closeness but she did say, “You must have been a good used car salesman because of that response.”

A few dances, another drink and a few more dances brought the evening to a close.

As they were saying their goodbyes Bill wondered what he could do to see Lynn again. He did mention when they were leaving the club that he was fulfilling his grandfather’s duties tomorrow by going to watch his oldest grandchild play soccer.

Lynn surprised him when she said, “Do you want some company?”

“Sure I do and that would be nice. I know where Cal lives so I will pick you up at one. I’ll bring the chairs but prepare yourself for the sun.”

‘Oh, I will.”

Bill was having some good thoughts about Lynn. That she volunteered to go to the soccer game told him she had some interest in him. Was it him or was it his fiancés she was interested in was something he needed to find out. No question she was intelligent and facially attractive as well as having a nice body. Was he catching her on the rebound from her divorce or was she catching him on his rebound from Traci? The answer to those questions needed to be answered.

In picking her up at Cal’s house, Lynn looked good and he told her that she did. Khaki colored Bermuda shorts and a light green blouse together with baseball cap and big sun glasses were her attire. The shorts she wore were just tight enough to show a nice jiggle to her ass when she walked.

Bill introduced Lynn to his son and daughter-in-law. He thought his son raised an eyebrow in meeting Lynn but he didn’t say anything or pry too much into her back ground. It really wasn’t much of a soccer game but it was fun to watch the kids. His grandson expended much effort in trying to score a goal. The game ended in a three three tie and while no one was supposed to keep score, everyone did.

After they said their goodbyes, they were in Bill’s Lexus. He said, “Where would you like to go to dinner?”

“Bill, I am not dressed to go anywhere fancy. Why don’t you decide as you know the area?”

“You are dressed fine and I was thinking about a Greek type family restaurant where the food is good and plentiful.”

“That sounds like something that would be nice.”

Dinner with Lynn was very enjoyable as she was very interesting person. The looks she gave him as well as the attention she paid to him told him something was developing between them. He thought that was confirmed because when they were leaving the restaurant Lynn said it still was early to call it a night.

Bill thought she was hinting at something but he wasn’t quite sure what it was. She had told him she was only going to be here for two more days before she had to head back to Clearwater. Knowing that he didn’t have much time to court her he thought he would see if the vibes he was getting from her were saying what he thought they were saying.

“I could take you back to Cal’s house and we could talk with them and maybe watch something on the television or we could go to my place and do the same thing.”

“Your place sounds better to me. If I know Cal, in a short time we would be talking politics, with each of us wanting to convince the other of our point of view. He isn’t going to change his views and neither am I, so your place is a better idea.”

There still was some doubt in Bill’s mind about what was going to happen at his place but not much. If he would bed her there was still a question, but it was something he looked forward to try and do. He thought by how she acted, she would be one exciting love partner.

At Bill’s place she passed on coffee but accepted his offer of a vodka tonic. She sat next to him on the couch. While the television was on, neither of them was paying attention to it.

Lynn finished her drink and putting it down on the coffee table she turned to Bill and placing her hand on his thigh said, “We have only known each other a short time. I find you to be a very interesting man and someone I would like to know better. Please don’t think I am being too forward but will you make love to me.”

“Does a cat have an ass?”

Laughing she moved toward him and said, “Yes it does and now kiss me.”

That’s all it took and they were off to the races. While they were kissing they were unbuttoning the clothes of the other. He unclasped her bra and heard her moan when his hand cupped a breast and teased its nipple. Her hand reached into his pants and stroked his cock.

“Can we go into the bedroom?” she asked.

He took her hand to lead her into the bedroom where they finished undressing and then they reclined on the bed. The kissing continued with their hands exploring each other’s bodies. His hand told him her most private part was shaven, warm and wet. Her hand told her his shaft was ready and no more preliminaries were necessary.

“Put you cock in me and fuck me. I am so ready for you to do that. Please don’t tease me anymore and fuck me.”

Some of the sophistication he saw in her was gone by her use of that language but it did excite him to hear her talk like that. Maybe that’s why she talked that way to excite him, not that he needed it as ready as he was.

As his shaft started to enter her she told him to take it slow as it had been a while since she did this. Bill was a little high but he still had his senses and felt his shaft go easily into her. He thought that either it wasn’t that long since she made love or she was so wet were the reasons he entered her so easily.

Her legs and her arms were wrapped around him. Vocally she knew what to say that further excited him. She told him how he was making her feel and that he was so good in fucking her.

Bill heard her say “Deeper... , harder... , deeper... , “ and finally “Oh my God, I am cumming.”

After she said this she gave him one long kiss with her tongue probing deeply into his mouth and he felt a sudden tightness on his shaft.

When this moment passed he continued with his hip movements.

“Again... , again... , do it to me again. You are... , you are... , I am coming again” and this time Bill joined her in coming with him depositing his warm spend in her.

They lay alongside each other letting their heartbeats return to normal. Her hand was on his now placid shaft with her thumb caressing its tip which was highly sensitive. It didn’t take long before it started to fill with blood again. Lynn helped the process as she moved and gave him great head. She was in such a position that he could put one then two then three fingers in her. She was wiggling her ass because of this and while she was giving him head she froze. With her forehead resting on his thigh she said in an exhausted voice that she was cumming and cumming again. Finally saying she could take no more, she removed his hand and resumed giving him head. When he came she swallowed every drop.

The time had flown by. It was almost eleven on the bedside clock and Lynn said she should be getting dressed and going.

“I wish I could stay the night but if I did the static I would get from Cal would be unbearable. He would not let me forget it. I can hear him constantly asking me what I did. He does take care of Joanna but he can be a big pain in the ass.”

Bill agreed with her and the both of them dressed. Bill drove her home and asked her if she wanted to go out tomorrow.

“Yes I do, but instead of going out why don’t we just do pizza at your place. I do like your place and we don’t need to go out.”

Bill agreed to that and received a kiss with a lot tongue from her before she left his car.

On the drive back to his place Bill had some mixed thoughts. No question Lynn was an exciting sex partner who knew what she was doing in making love. She enjoyed herself and made sure Bill also enjoyed himself. The thing that bothered him was that it didn’t take long for him to bed her. In fact it was her idea that they should make love. He knew he was an average looking guy, well maybe a little better than average as he chuckled to himself. He realized that it didn’t take much effort to bed her. He wondered if there was something going on that he didn’t know.

The next day he picked Lynn up and they did do pizza at his place along with adult drinks. Without anything being said she took his hand and led him to the bedroom where they made love again. This time Bill worshiped at her shaven mound which had Lynn going ballistic. That she would react as she did made Bill wonder if there wasn’t anything she wouldn’t do.

He put one finger then two into her rosebud and she never said anything and only moaned. He moved up to her and placing her calves on his shoulders he was able to raise her hips enough to where he could insert his shaft into her rosebud. Again there was no objection from her as he was doing this and in fact she helped by spreading her butt cheeks. The only thing she said was “So big... , so big.” He came with his spend going into her chute.

They were cuddling afterwards when Lynn said, “It has been a long time since I made love that way. I am going back to Clearwater tomorrow. I am going to miss this and you. You are a great lover. Maybe you could come down and visit me sometime? You said you are going to be wintering in Florida. Why not do some of your wintering in Clearwater? I can show you around and we can do some other things that I think we both would enjoy.”

Giving a playful tug to his shaft she said “I will make sure you would really enjoy yourself.”

“I know I would and will think about doing it. You are an exciting woman who makes me feel good that I am a man.”

Again Lynn said she was sorry she couldn’t stay the night because of Cal, but that would not be a problem if Bill was to come to Clearwater.

Dropping Lynn off at Cal’s house he again received another long kiss that had her very active tongue probing his mouth. What was a little different this time was that Lynn placed his hand on her breast as he was kissing her.

Driving home he thought that she was one hell of a woman. Stopping in Clearwater for him seemed to be a no-brainer.

The next day Bill left work before noon and went to the club to golf. He golfed with Ken and Greg and shot his usual score. Walking into the clubhouse after the round he saw Cal who waved him over.

“How did it go with Lynn?”

‘It went fine, she is an exciting lady.”

“She is my sister-in-law so I shouldn’t say this but you are my friend. That puts me in a difficult position but I need to tell you this. Lynn was married to Josh who in my opinion was a pretty nice guy. Before they got divorced I had spoken with him and he told me they were having a tough time. He said that Lynn was extremely money orientated and Josh was told by her that he wasn’t making enough money for her to live the life style she wanted. That probably was the reason they divorced.”

“Compounding that is that I overheard a conversation Lynn had with Joanna that I wasn’t supposed to hear. Lynn said that she liked you and she thought you could provide the lifestyle that she wanted. Take that for what it’s worth but I thought you should know.”

Bill thanked Cal for the information. He made a mental note that he wouldn’t be stopping in Clearwater this coming year no matter how good the sex would be.

At the dealerships business was progressing normally with no major problems. Bill thought that hiring good people who had pride in how they handled their duties and complimenting as well as rewarding them were the keys to his success in managing the business.

Claire had gotten the car rental operation off to a good start. Referrals from insurance agents and insurance claim departments because of the competitive car rental rates they offered were causing her to expand the number of cars and mini vans they rented. She proudly told him that in the first three weeks she had sold five used cars.

He kiddingly told her that her bonus this year would probably put her in a higher tax bracket.

Her response of “I can live with that” caused both of them to laugh.

With time on his hands Bill started to think of where he would winter in Florida this year. His friends had recommended places they liked that were both on the east and west coasts. While Bill trusted his friend’s recommendations, he would like to have a little more information before he made a decision.

He then remembered what Lynn had said about a cruise during the summer and the number of single women, mainly teachers that took cruises at this time. He had never taken a cruise but a number of his friends had and generally recommended this type of vacation. His passport was current so he thought why not and started to search the internet for more information.

If he did go to Florida and take a cruise he could also scout out the places that were recommended to see if these were places he would want to winter in. Maybe splitting his time between places on both coasts was another option he should consider doing.

Bill spent most of the afternoon on the net and learned a number of things. Depending on the port the cruise ships left from, the places the ships visited were generally the same no matter who the cruise line operator was. Also the prices of cruises were two tiered from reasonable to expensive depending on the cruise line. While a few ships were accommodating to single passengers, most were not. Acknowledging he could afford the single supplement he booked an outside cabin on a six night cruise that left from Tampa. The ports of call were Key West, Cozumel, Belize and Grand Cayman.

After booking the cruise he went back on the net and booked his flight down to Tampa.

Preparing for the cruise brought Bill a sense of anticipation that he enjoyed having. His friends volunteered a lot of do’s and don’ts.

Finally that day came and after an uneventful flight and the cattle call of boarding he walked on to the ship. He took the time to walk around the three main floors where the lounges, restaurants and casino were located. His first stop since his room wouldn’t be available for two more hours was on the Lido deck where he sat and ordered a drink. He noticed that a number of his fellow passengers were already feeding their faces. Some of them to put it bluntly could stand to miss a few meals but he had been told that some guests measured their enjoyment of the cruise by how much and often they could eat.

What he also saw was that there did appear to be a large number of unattached women that ranged in age from twenty to seventy. He also noticed that some of these women were giving him a good looking over.

Finally he was able to enter his cabin he was surprised that his luggage had already been delivered being place at the cabin’s door. He also noted that the two beds had been placed together as he had requested. He asked for that because he hoped to get lucky on this cruise and find a woman to bed. After unpacking and washing up he left his cabin and went to the martini bar to have a drink till it was time for dinner. Bill had signed up for the early dinner seating and hoped he would have some enjoyable dinner companions.

The first stroke of good luck had on this cruise and he hoped there were more to come, was when he was shown to his assigned table which was a table for eight people. Of the seven people there besides Bill, were a young couple that was on their honeymoon, and older couple who said they were retired, and three women he learned that were teachers. The women introduced themselves as Liz, Zoe and Cora. Bill made a point to memorize their names. The ladies seemed to be a few years younger than him and were fairly attractive. The best looking of the three in his opinion was Cora, a blond haired lady. If he could bed one of the three on this cruise, that in his mind would make this cruise a success.

Introductions were made and the conversations revolved around on where everyone was from and what they did. Some of the tours available while in port were discussed. The older couple were cruise veterans and gave everyone their recommendations as to which tours to take and what to do or purchase when in port. Overall it was a good dinner highlighted by Bill purchasing some wine for the table to toast the honeymoon couple.

All of his dinner companions seemed like nice people and were excited to be cruising. Maybe Cora was a slight exception to that. There just was something he sensed that was bothering her because of how she was acting.

After dinner Bill went and caught the show in the main theatre. It was the ship’s singers and dancers who put on a show with a Mexican theme. It wasn’t a Broadway quality show but it was a good high energy show. After this show Bill went to the lounge and debated if he should stick around to see the scheduled entertainment of a comedian that would be there in forty five minutes or do something else.

Hearing “Hi stranger” he turned to see Liz and Zoe standing there who were two of his dinner companions.

Bill stood and offered to buy them a drink.

Liz said thanks but they were going to go up to the Sky lounge which was less crowded than this lounge and listen to the danceable music the band played there.

“Well I can just as soon buy you a drink there and if you don’t mind I will keep you company unless that presents a problem.”

Liz said, “Oh, it presents no problem at all. Single men are like gold on this cruise so please come with us.”

He was hoping the “come with us” was a forecast of things to happen.

They sat at a table in the lounge and Bill ordered the drinks. The band was playing danceable music. There was something about the looks he was getting from both Liz and Zoe that told him they could be available for some serious love making. He asked Liz if she wanted to dance and she accepted his invitation.

On the dance floor Liz had her body right up against his. She was not bashful about doing this and that just seemed to confirm to Bill that she was available. He danced two slow dances with her and started to become aroused which he thought she could feel by how her stomach was pressed against him.

Back at the table he had his drink and then asked Zoe if she wanted to dance. Zoe was a little cautious in how she danced till she caught his style of dance but then she like Liz was right up against him.

When the band took a break Bill excused himself to go to the restroom as the drinks were starting to go through him.

In coming back to the table it seemed to him that Liz and Zoe were having a serious discussion but that it ended when they saw him.

About a minute later Zoe said “I guess I am having some jet lag because I am beat. You kids have some fun but I am going to the cabin. Enjoy yourselves.”

Something seemed to be going on between Liz and Zoe. Bill did have some suspicions that there might have been a coin flip and Liz won the flip as to who would be with him. It just wasn’t his male ego saying this but he felt that this opportunity to be alone with Liz had been staged.

He thought his suspicions were proving to be correct when he went back to the dance floor with Liz. This time both of her hands where over his shoulders and she was pressed against him as they slowly danced. He now was curious as to how she would go about it as it seemed to him they would wind up together in bed. Was he supposed to do something or would she? He thought he would give it some time to see what would happen.

When the dance ended she moved her head back a little from Bill and when right for the jugular. She knew what she wanted and simply said “Why don’t you show me what your cabin looks like since you have an outside cabin and mine is an inside cabin. I would like to see what it looks like.”

There was not a doubt in Bill’s mind as to her wanting more than just wanting to look at his cabin. He would put money on what was going to happen when they were in his cabin. It turned out he was correct. She went to look out through the porthole to see what if any was the view at night since she was staying in an inside cabin.

This enabled Bill to plug in the nanny cam that was motion activated. After the incident he had in Tucson where he was falsely accused of rape he wasn’t going to take any chances and would record his love making sessions when he could. While it may have been against the law to do this, the ramifications of not doing it he had learned could be much greater. What if anything was the law at sea about doing this recording was something he only briefly wondered about.

After confirming that at night there wasn’t much of a view out of the porthole Liz came back to him and started kissing him. Her hand dropped and massaged his package with her giving a slight moan as she did that.

Turning her back to him she asked him to pull down the zipper on her dress. He did and since the light in the cabin was still on he could appraise her body. She had a body that you would want to cuddle with all night. Her breasts were of nice size but he thought her ass did have a few miles on it. As she took off her thong he could see that her mound was almost cleanly shaven with only a little tuff of hair above it. She reclined on the bed waiting for him to finish undressing. He did and turned off the lights in the cabin but turned on the light in the john which gave a subdued lighting to the cabin, He joined her on the bed.

 
There is more of this chapter...
The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.

Close
 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.