This true story is written by me and my wife from our experience with Big Uncle Jim. From the time we got married, my Uncle Jim would tease that someday he was going to bed my young wife Karen. We would just laugh it off. After all, Uncle Jim was a large and old 60 and Karen was a hot 24. After a while, it became apparent that Jim was serious. I found myself thinking that if he could actually pull this off, I would let him. With the odds stacked against him, I even started rooting for him at one point. If we went somewhere that Uncle Jim would be there too, I would ask Karen to wear something sexy just for him. Karen wasn’t into him, but she would do it anyway. One day, Uncle Jim bet me $1000 that he could bed Karen in 6 months as long as I promised to not interfere. I agreed.
In a few months, Uncle Jim approached Karen with a proposal. He was an amateur photographer and wanted to enter Karen’s pictures in a sexy pin up girl calendar contest. Each picture selected would be worth $500. Jim believed that he could get 2 pictures of Karen submitted. She agreed as long as I went along.
The next week, the three of us met at a friends’ cabin on a lake for the weekend. We got there Saturday morning and Jim and Karen got to work. He took very sexy pictures of her in swimsuits, and shorts, and miniskirts. Later in the day, he had her modeling lingerie. That was the most that Karen had spent with Jim and she found him very charming once she got to know him. As the day progressed, Uncle Jim became very attentive to Karen which made her feel special. She let him pose her in various positions that would be both innocent and sexy all at the same time. Karen got more and more comfortable with Jim’s huge hands on her, fixing her hair, moving her arms, legs or shoulders for just the position. I was moving lights and cameras and furniture around to get the right effect. It was funny to me to see Jim be so attentive to Karen like she was a little glass doll. Uncle Jim stands about 6 foot 5 with very broad shoulders and even a beer belly. Karen is a very petite 5 foot 1 and is about 105 lbs. If he wanted, Jim could pick her up with one arm.
After dinner and some more picture taking, it was time for bed. Problem was that we just now found out that the guest bedroom had no furniture in it at all and the nearest hotel was at least an hour away. The couch was too small to sleep on and the floors were all hard wood and there were two other chairs, but neither of them reclined. Karen stated the obvious that all of us would have to sleep on the king sized bed in the master bedroom. I thought that Uncle Jim was going to jump for joy when she said that, but he stayed pretty cool about it. Certainly Jim’s bet wasn’t going to take place tonight with all of us in the same bed. When Karen got ready for bed, she came out in a simple white cotton gown with buttons up the front. The gown only went down to her mid-thigh. I could tell that, as usual, Karen wasn’t wearing anything under her gown. When she walked in front of any light, her silhouette would show through the gown and show everything underneath. I saw that Jim was noticing too. I then went to get ready and put on a t-shirt and gym shorts. Then Jim went in and came out in his boxers and tank top. We stayed in the living room and talked for a while and watched TV. Then I was just too tired to stay awake and went to bed. I figured that Karen would sleep between the two men so I took one side of the bed and dozed off. This next portion is written by Karen.