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.
Ron went to bed, and I stayed up talking with Uncle Jim for another hour. He was very funny and we talked about the pictures he took of me earlier in the day. He loaded them onto his lap top and we looked at them to see which ones we wanted to submit, which ones needed a little photo shop and which ones needed to be redone completely. It was kind of erotic watching him looking at me in those sexy outfits and poses and knowing that these could be put on a calendar for other men to see as well. I was getting a little turned on by it all and a couple of times, I caught Uncle Jim noticing my nipples getting hard through my night gown. I even noticed that Uncle Jim was getting hard and trying to hide it. Not knowing what else to do, I said it was time for me to go to bed too.
I crawled into the bed next to Ron and heard the heavy steps of Uncle Jim coming down the hall. Ron had turned the bedroom lights off, but there was a full moon and it lit up the room through the two windows. When Uncle Jim walked over to the bed, I could see another reason why the called him “big Jim.” I wasn’t trying to look earlier, but the end of his cock was down below the leg of his boxers. Even in the limited light, I could tell he was at least 12 inches long and he wasn’t even hard.
Uncle Jim crawled into the bed and I told him that I had fun being a model for him. We faced each other talked in hushed tones for a bit and then I noticed his hand on my arm. He was lightly rubbing it. I didn’t know what to do, so I just kept talking. He then massaged my shoulder and soon, his hand went down my side to my waist. His hand felt like it nearly went all the way around me. As we whispered and I ignored his touches, his hand moved to my stomach and I felt him slowly find the buttons to my gown and start to undo them. I felt like I was frozen and didn’t know what to do. I didn’t want to wake Ron and cause a scene, I didn’t want to embarrass Uncle Jim, and yet, this was both exciting and dangerous. I chose to continue to ignore Uncle Jim’s nervous progress until he got to the last two buttons at the top of my gown. I felt me hold my breath as first one button and then the last was finally released. Uncle Jim then slowly pulled open my gown and moved the top of it over my shoulder. He then pulled back the sheet so that he could see me. I watched him study my breasts before he put his hand on my shoulder again. I was a bit surprised when he moved his hand to the back of my head and smoothly brought my face to his and kissed me. He was very gently and yet purposeful in guiding me. Our kiss went from soft and sweet to passionate as he moved his hand to my breast and explored me. I couldn’t help but hold onto his massive arm. In a moment, Uncle Jim took my hand and guided it down his chest, onto his stomach, and then down to his cock. It was now huge and not even all the way hard yet. My hand seemed to take on a life of its own as it explored the head and the veins and down to his balls. I could feel it grow even larger at the touch of my hand. As I stroked him, I noticed that my fingers barely went all the way around. We kept kissing and then Uncle Jim took his hand to the center of my back and pulled me closer. My breasts were right up against his chest. Jim then pulled my leg over his hips. His tongues explored my mouth as his dick tried to explore a way into me. He was so large that it didn’t go right in, but rather pushed along until I was completely straddling it. I could feel it throbbing against me as if it was breathing on its own. I couldn’t help myself, so I slide my hand down my bottom and felt the head of Uncle Jim’s cock protruding beyond me. If we had been standing, I could have fully sat on the shaft of his cock. I was so wet and turned on, I couldn’t help but moan softly.
Uncle Jim must have taken this as a good sign and laid onto his back then slid his other hand to underneath me and easily moved me to be on top of him. My legs startled him as he put his hands on my hips and moved me around as we kissed. Finally, Uncle Jim had me where he wanted me. I could feel his huge cock pushing up against my wet vagina. Uncle Jim’s powerful hands moved my hips up and down against the head of his dick as it tried to enter me. I whispered that he might be too big for me and to take it slow. Uncle Jim pulled me up onto his chest so that he was sucking and kissing my breasts. I moaned again as I felt like I was nursing this huge man. Uncle Jim then took his hand down my side and slide it down between my legs. His middle finger found my clit and when he started teasing me there, I must have poured out onto his hand. I couldn’t help but push hard against his finger. He moved his finger inside of me and it actually felt like the size of my first boyfriend’s penis. I came again while his massive hand held my by my vagina and had another hand on a breast and his mouth on my other breast. When he released his grip on me, Uncle Jim moved my hips again to push me down against the head of his penis. I kissed him again and he was so intent on being inside of me, Uncle Jim reached down again with his hand to help guide the way. As he parted the lips, I moved my hips around to help him. I felt the head of his penis up against the opening. I whispered, “please take it really slow.” He kissed me again and laid still while I slowly slid myself down his shaft. Little by little, I moved up and down his shaft going farther and farther with each push and pull. I then whispered, “wow, I can’t believe it, you’re actually in me!” Then he whispered back how good I felt. With Uncle Jim’s cock inside of me now, I slowly sat straight up and let him massage my breasts while I rocked my hips back and forth and slid up and down on his shaft. It both felt good and hurt a little all at the same time. Uncle Jim pulled me back toward him and then kissed me. As he held me, he turned me over so that now I was on the bottom and had Uncle Jim on top of me between my legs. He pushed and pulled himself inside of me and I heard myself whispering, “deeper! go deeper!” I could feel his cock swell yet again as his thrusts became harder and more purposeful. Suddenly, Uncle Jim’s cock exploded inside of me and I came too. His sperm kept pouring into me as he would thrust, then pause, then thrust again. I was so exhausted by taking it all in and keeping pace with him, I could barely move.
When he was finished, Uncle Jim got up and handed me a towel to put between my legs. He whispered that it had been a long time for him and he had a lot of build up. So I might be leaking for a while. It was more like a day! Later in the night, I felt Uncle Jim get wrest less and then felt his cock up against my bottom. He was getting hard again and looking for a place to put it. Uncle Jim’s cock slide between my legs. I felt down there and it seemed like I had my own penis sticking out between my legs. Uncle Jim reached around me to pull my leg back on top of his, then he rubbed himself again against my vagina to get me wet. I whispered again to go really slow. It took some help from me, to finally get the head of his massive penis to just inside the lips of my vagina. Then Uncle Jim very slowly pushed himself inside of me. I could feel the throb again. Uncle Jim massaged my breasts as he slowly pushed his hips against my bottom. When he came again, this time, he left himself inside of me. It must have been an hour later when I woke up and he was still penetrating me and throbbing. Uncle Jim was sound asleep.
Added by Ron and Karen
