I guess I should start out by telling you that I am 54 years old, and my wife of 28 years just died a year ago. I have been a successful insurance salesman for 30 years. In that time, I made a lot of money and I have been investing it all along. I am now worth several million dollars but no one except my wife and my stock broker knew that. I now do my investing on-line so no one but me knows what I am worth. My wife and I never denied ourselves anything we really wanted but we have lived modestly. We have a 15 by 30 pool in the back yard and a cabin in the mountains, but other than that nothing everyone else doesn't have.
My sister Kate, who got pregnant and married at 18, and her husband have always lived from paycheck to paycheck. Sometimes his foolish spending or gambling would get them in financial trouble and I would find out about it. I tried to make it clear to her that I had more money then she would think, and that any time she got in trouble financially she should let me know and I would help her out. She only asked for help a couple times when she really needed grocery money in order for her and kids to eat. We had always got along even as young children and teenagers. I never considered her little pest or pain in the ass, she was always my little princess. I used to help her out with her school work, protect her against boys that were becoming obnoxious. We always got along very well, and I did love her, but as a sister. We never did anything sexual while we were young.
If you were to see my sister in the mall you would probably not even notice her, she is average height with mid length brown hair, and wears baggy, loose fitting clothes. There is really nothing about her that would attract attention to the casual observer. Understand there is nothing unattractive about her, she is just a plain Jane. That is from outward appearances, when you know her she is a beautiful person. She is always upbeat and fun to be around. Over the years I have seen her in a bathing suit in our backyard pool and I can assure you she has a fantastic body, very nice tits and a nice round little ass. Since she has been living here I have frequently seen her in her tight fitting workout clothes. She works out every day for at least an hour. When her kids were younger her daughters used to kid her son, because mom could do more pushups than he could. I once saw her rip off 30 pushups without slowing down. When fixing breakfast she often times passes between me and the light pouring in the kitchen window, which makes her otherwise decent pajamas practically transparent. I have on several occasions found myself thinking, I really would like to fuck that woman. Then I have to give myself a mental slap for thinking about screwing my sister. The thoughts have come more and more frequently lately, and the slaps less severe.
Anyway her husband, Jim, died three months ago. After the funeral everyone came to my house because she and Jim lived in a one bedroom apartment, and there wasn't really enough room for the typical after burial gathering. Her 3 children had all married young and were starting down the same paycheck to paycheck existence that their parents lived, so they were not going to be able to help her out. As we were sitting around talking, her oldest daughter mentioned that she would have to find a new apartment since they had gotten a eviction notice. It seems Jim had bet the rent money on a football game.
I told Kate not to worry about finding a place to live since I lived in a three-bedroom house all by myself. I told her she could stay with me until she got back on her feet. We decided that she might as well start staying that night rather than going home to the empty apartment, and spending the night alone. Everyone agreed that probably would be a good solution to her problem. After everyone left we watched a movie on HBO, then she went to bed in the guest room that she had picked out for herself. I had piece of cake and a glass of milk and then went to bed myself. I was unable to fall asleep immediately, and was still awake when about 15 to 20 minutes later Kate knocked on the door.
After she came in she asked me, could sleep with me tonight and please hold her. She said she was scared about the future and didn't know what was going to become of her. She had never been anything but a wife and mother and had no idea how she was going to support herself from now on. I knew that this was totally innocent request, she only needed comforting. So she got into bed and laid with her back to me, and I held her. I told her to stop worrying about her financial future that she would have no financial problems from now on. I had, and I'm sure she had no indecent thoughts about the sleeping situation. However when I awoke in the morning I had my hand on her breast, and it was a handful, with what felt like very large nipples, and a hard on pressed firmly against her ass. I immediately knew that she was awake, but wasn't doing anything about it for fear she would wake me up in this embarrassing position. I made some noises and rolled over as though still asleep. She immediately got out of bed and went to the kitchen. A few minutes later I could smell coffee brewing. I got up and when to the kitchen and said that the smell of coffee had woke me up. We each had come coffee and she fixed breakfast for both of us. That was the only thing of a sexual nature that happened between us for the three months that she lived with me prior to her birthday.
I had seen enough of her to appreciate the fact that she had an excellent body had it to a belonged to a 20 year old girl. For a 50 year old woman she was out of this world fantastic. Anyway on her birthday I decided to take her out to celebrate. We left in the late afternoon and went to a indoor miniature golf course that also had arcade games. We then went to dinner at a local surf and turf restaurant. Before dinner I had a couple martinis, and she had a couple Manhattan's. We had wine with our dinner, and one after dinner drink each. From their we went to a private club that I belong to. It's a dimly lit cheaters kind of place. They have a small group there on Saturday nights that plays, old sexy romantic dance music, the type of songs that Julie London might sing. We had a couple drinks and did some dancing.