This is Part 1 of a 3 Part Story. Although I have had similar experiences, the names, characters, businesses, places, events and incidents used in this series are either the products of my imagination or used in a fictitious manner. The physical descriptions and occupations are purely fiction. Any resemblance to any real persons, living or dead, or any real place or actual events is simply coincidental.
Day 1 contains much of the back story and set up. It will help you understand the people and the setting. If you are all about the sex, you can skip to Day 2, but I am hopeful that readers will find the whole story interesting.
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It has been over 2 years now since my father-in-law passed. It was not unexpected, but it was difficult for my wife, Terri, and her mother, Ruth. It was particularly difficult for my mother-in-law as she was left as a widow all alone in a large house. While Ruth and my father-in-law had made friends in their neighborhood, most of their friends were couple friends. Every day, she was feeling more isolated and lonely. After much discussion and thought, my mother-in-law decided to sell the house and move to a retirement community, The Residences, in Orlando, Florida. She had heard many good things about the community, and had visited a number of times before she finally bought her new house. Ruth purchased a house in a "middle of the road" portion of The Residences, but she had access to all of its various communities and golf courses. For someone like my mother-in-law, The Residences is an amusement park for the retired.
While Terri had visited her mother on several occasions, I had avoided making the trip. Ruth and I did not necessarily dislike each other; however, I would not say we are close. Over the 25 years I have been married to her daughter, Ruth and I developed a passive indifference to each other. I found that our relationship is best kept at a distance, and any in-person visitation was kept to a minimum. My ability to avoid visiting my mother-in-law was getting more difficult with each trip Terri took. During her trips to The Residences, Terri would send me pictures of the community and tell me how wonderful she thought it was. She would often tell me how she would like us to move there once we retired from our professions. From the pictures I received, the place looked beautiful, and it had so many activities to offer, including all the golf you could ever want to play. When Terri returned from her last trip, I knew that there would be no way I would be able to put it off any longer. So, the following June I flew to Florida with my wife to visit Ruth.
Day 1.
Ruth picked us up at the Orlando airport. She was thrilled to see her daughter again, and did not seem to mind that I was there as well. After the perfunctory hug Ruth and I always gave each other, the three of us headed to baggage claim. While waiting for our bags to arrive, Ruth explained to me that she had made several new friends, and that she had set up a dinner for us to meet a few of them that evening. Terri smiled at the news having met Ruth's friends before. Ruth also told Terri that she had been putting off shopping for a few furniture items until Terri could help her. They both assured me that I would not be required to go furniture shopping, and that I would have a few days to play golf, lounge around the pool or simply take it easy doing nothing. Feeling that I was wasting a perfectly good vacation, I smiled my best smile and went to retrieve our luggage.
The trip from the airport took just over an hour, all of which was spent filling me in on all the things that The Residences had to offer: pools, country clubs, restaurants, movie theaters, and golf courses. The community is divided into town squares, each with its own dining and shopping area. The primary mode of transportation is by golf carts, but not your normal golf carts. Most are tricked out and contain many comforts of a car. While there is a fairly active nightlife, including live music every night, most things are shut down by 9:00 each night. I have to admit, the more I learned about the place, the more I thought I could make myself enjoy the time. The community had a minimum age limit of 55, with the average age of the residents being in their early to middle 60s. Having recently turned 50, I felt like a youngster. I work hard at staying in shape, working out, running and swimming 4-5 days a week. I am 5'11" and weigh 180 pounds. I do not have a six-pack, but I don't have a beer gut or love handles either. I still have most of my hair, which has remained a light shade of brown, with maybe a hint of grey here and there.
As I listened to Ruth and Terri talk about her new friends, my hesitations began to dwindle and my interest was definitely piqued. That evening we were having dinner with Mary, Joyce and Kathy. Mary and Joyce were both single. Mary's husband died two years earlier, and Joyce had been divorced for over three years. Apparently, Joyce's husband of almost 35 years left her for a much younger woman. Kathy was married to Bill, but Bill was never around. He spent his days on the golf course and his nights out with his friends drinking and playing cards. The rumors on the street were that Bill had a few ladies on the side, something that is not unusual in this community.
Ruth had met Mary and Joyce at a dance class that she took every other Thursday night. I could not help but smile when Ruth told us that Mary is a former Las Vegas showgirl and Joyce was once a college cheerleader. Ruth said that both of the women had "aged well" and that they were highly sought after by many of the men. Ruth said that Kathy was also very attractive, but always seemed sad. Kathy and Joyce were close, so Joyce would often ask Kathy to join them whenever they went out. Ruth told me not to worry, that although I would be the only man at the table, Joyce and Mary told her they would make sure I was included in the conversation. I did not tell Ruth or my wife that I was not worried, but that I was actually looking forward to being the only man at a table of women, especially after the descriptions Ruth had given me.
As we entered the gates and drove through the community, I was amazed at the size of it. It seemed to go on and on, with a pool, clubhouse or golf course on every other corner. Ruth's house was a cute little three-bedroom ranch, with a nice screened in porch. Ruth had decorated the house tastefully. She showed Terri and me our room, and then told us we needed to get ready to head to dinner. I was a little taken aback as it was only 5:00 p.m., and I was not really hungry. Ruth must have seen the look on my face. She explained that most people ate rather early so they could take part in the activities at night, including the live music. I took a quick shower and changed into something casual but dinner appropriate. I drove the three of us to dinner in Ruth's golf cart, and parked between a baby blue "t-bird" golf cart, and a "fire truck" golf cart. We walked in the restaurant around 6:00, and I noticed that it was not only packed, it was hopping. A band was playing, and people were eating, drinking and dancing. The atmosphere was one of celebration. I was immediately put in a good mood.
I saw Ruth waiving and looked in the direction of her gaze. I was in awe. Standing up and waiving was a stunning woman, tall and slender, with what appeared from a distance to be absolutely perfect breasts. I knew immediately that I was looking at Mary. Mary is brunette, maybe with some help from a bottle, and she is beautiful. As I was introduced to Mary, I noticed that she is tall, around 5'10", and she is in tremendous shape, and not just for a 63 year-old woman. She wore a summer dress that accentuated her curves and loosely clung to her breasts, which were no doubt a solid D cup. Her breasts were definitely on display. I did my absolute best not to stare, but felt that she was used to getting attention, both from men and women. I looked over to Terri who was smiling at me, knowing very well that I was trying not to look. I reached out to shake hands with Mary, who shook her head and told me she was a hugger. As we hugged hello, I felt her breasts against my chest. The almost instant reaction from my cock surprised me, but hopefully, did not betray me. I reluctantly pulled away allowing Mary to move toward Terri, giving her a hug as well. As Mary passed me, she quickly glanced down at my crotch and then looked back up and winked at me. Did she know? Well, nothing I could do now.
Mary introduced me to Joyce and Kathy. Joyce is 65 years old. She is around 5'6" with a slender build. She did not have the curves that Mary had. She had smaller hips and breasts, but looked like she worked hard to maintain her figure. She is blonde with beautifully expressive blue eyes. She has an award-winning smile and a very flirtatious and outgoing personality. Joyce is also a hugger, and I was really beginning to enjoy this. Kathy is 66 and attractive. She is around 5'5", and while she is a few pounds over her prime, she still looked good. What you could tell the most about Kathy was that she came from money. She was dressed impeccably and expensively. Her clothes fit her well and accentuated her body wonderfully. I later found out the she and Bill had been "in the market" in New York before they retired, and they did quite well. They lived in the most expensive area in the community. Still, there was a sadness that you could feel from her. She was not a hugger, so I shook her hand as we were introduced. As we sat down, I ended up between Joyce and Terri, with Mary on the other side of Joyce and Ruth sitting next to Terri. Kathy sat on the other side between Mary and Ruth.
Mary, being the cruise-director type, made sure we all ordered a drink and toasted our arrival and their friendship. Throughout dinner, Mary made sure that everyone had a fresh drink at all times. As dinner progressed, Terri and Ruth talked with Kathy about the furniture Ruth wanted to buy. Kathy knew a lot about the local market, and she suggested a few stores in Winter Springs, Florida, an affluent part of Orlando. I zoned out of this conversation and was brought into a conversation with Joyce and Mary. It started with general conversation about who I was, what I did, and where we lived. I asked them questions about their backgrounds and how they ended up in Florida. They both talked about coming from warm climates, with Mary being from Las Vegas and Joyce being from Arizona. They both loved the warm weather that Florida offered, and loved the activities that were available to them at The Residences. Mary said that it was near perfect, except for the lack of available men.
Apparently, although there were plenty of men, many were married and their wives did not like Mary around them. Mary said that there were a lot of single men, then winked, whispering, "the question is whether they are fully functional." Joyce laughed and playfully slapped Mary, then squeezed her thigh. This was not the first time I noticed that Mary and Joyce shared a lot of familiar touches.
Of the single men that were "functioning," most did not want any commitment. Although the community is large, it is small enough that reputations were easily obtained. Neither Mary nor Joyce wanted to be known as "those types of women," so they dated sporadically.
