I was 33, balding and I weighed too much at 200 pounds. When I hang out with Greg my self-image is pretty good. Greg is about 5 years younger than me and works at the brokerage that I worked at before I got rich on a tip from a customer. Greg takes care of the details of my finances now as my Trustee. Most days I follow the markets and call Greg with my thoughts on what is about to happen on the markets and he uses this information to make money for his himself and his clients. Greg and I go to most sport events in town and usually get together once or twice a week just to hang out. He is a really nice looking fellow who is always going out on dates with beautiful women but he rarely dates them for very long.I guessed that my lack of happiness was due to my relationship with Janet. She is 2 years younger than I am. She is attractive but not beautiful. We have been dating for about two years. We had a great sex life until about three months ago when she appeared to start to lose. By the time we were fucking on the tape I had lubricated Jenny’s bum and was rubbing the head of my cock over her arsehole. When Gary penetrated me on the tape I pushed my cock hard against her sphincter. Jenny came as my cock slid up her arsehole crying out and gripping the beanbag. Her eyes never left the action on the TV. I fucked her tight arse, keeping pace with Gary on the video, dragging my nails down her back. Jenny pushed one hand under her and pushed three fingers into her cunt. I lent over her and grabbed her hair, pulling her head back. ‘Do you like my cock in your arse babe?’ I said fucking her with short, hard strokes. Jenny answered by orgasming again, her arsehole clenching on my cock and making me cry out in pain and pleasure. I felt my orgasm building as I watched Gary pull his cock out of my arse on the video, pull me down in front of him and spray my face with cum. I pulled my cock out of Jenny and sprayed her back with semen, slapping my cock on her fleshy.
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