I've read a number of stories here about brothers and sisters, dads and daughters, etc. The only family member I've done this with is my aunt.
I have always loved my aunt. I've always found her pretty and sexy. She is about ten years older than me. When I was 38 I confided in her that I found her extremely sexy and I thought about her often. She was very surprised to hear this, but she smiled warmly at me and gave me a warm hug.
Maybe a month later, one day we were talking on the phone and I asked her over. It was in the middle of the afternoon and she had nothing to do so she came over to visit. We sat in the living room on the couch and talked, eventually I again mentioned how much I thought of her and how she 'did something to me.' I was getting hard talking to her like this and I just went for broke. I cupped my hand over the bulge in my pants and squeezed myself. Her eyes followed the action of my hand. I guess she was sitting there not knowing what to do or what to say.
I told her I had had sexy dreams about her for many years. I was so hard at this point. She said she was flattered and some things like that. I got really bold and spread my legs and started to mock jack myself on the outside of my pants and I told her I had done this probably hundreds of times as I thought about her. She was still hardly saying anything. Maybe just in shock? But she wasn't leaving or telling me to stop.
I had on a pair of shorts because it was summer. I decided to really go for broke and I said 'I hope you don't mind...' and I unbuckled and unzipped and pulled my shorts and underwear off in one swift movement. My dick was probably the hardest it has ever been. I just looked at her and started slowly feeling myself and slowly jacking myself. Again, I told her how much I loved to do this while thinking about her.
She finally said something like, 'Oh my. You are really hard aren't you.' I told her yes, and I told her I had made love with her in my dreams so many times...and I wanted her so badly. She kept her eyes glued to my dick. I finally said, 'I love doing this in front of you, are you sure it's OK with you?' She told me she was actually liking it. I asked her if she had ever had any sexy thoughts about me since I gushed a month earlier that I found her sexually appealing, and she said, in fact, since I had said that she had thoughts.
I was really hot, hard, and excited. I asked her if she would do me a favor and take her clothes off so I could see the body I had dreamed about for years. She hesitated for what seemed like an eternity, then finally said OK. She stood right in front of me and stripped naked. I almost came when I saw her. Oh my, what beautiful bare breasts and suckable nipples...and her pussy, oh my gosh, black pubic hair surrounding gorgeous lips. I got off the couch and held her in my arms so I could feel her totally naked body against mine. Her hands found my dick and my fingers found her slick pussy. We stood and fingered and jacked for a while. I asked her to sit on the couch and spread her legs wide for me and she did. I turned sideways on the couch and spread my legs so she could have a great view of my dick and balls, and I started jacking as I told her how beautiful she was, what a dream come true this was, how badly I wanted her, how beautiful her breasts and pussy were, as she rubbed her clit and fingered her pussy. My aunt, my gorgeous aunt who I had beat off thinking about for years was naked in front of me fingering her pussy. It was overwhelming. I can't remember how long we did it but ultimately I knew I had to squirt my cum. I asked her where I should do that and she asked me to do it on her tits, so I stood beside her and emptied myself on her breasts, and about then she came shuddering and shuddering.
We cleaned up and I held her closely and kissed her warmly and told her that had been the most erotic, exciting, intense thing that had ever happened to me. We discussed that it was basically wrong though. I tried another time to get her over but she made an excuse. I haven't tried since, but I have jacked off a thousand times thinking about that day.