I'm a widow and my husbands oldest sibling Dan is 67 and a widower. I stayed close to all of my husbands family after he died 12 years ago.
My husband died suddenly without warning and I was devastated at his death. My only son now lives in New york but I do see him and my granddaughter several times each year. My husband was dead five years before I ever dated again and none of the men I did date and have sex with were ever close to my heart. I kept in touch with Dan over the years and it was my sister-in-law who more or less talked me into moving in with Dan. It had nothing to do with sex since Dan has been impotent for many years. We became very close, cried on each others shoulders and shared everything with each other over the first year or so. I hadn't dated anyone in a long time but did masturbate fairly often and one night Dan caught me. It was the first time he ever saw me naked and to make matters worse I was using a vibrator on myself and at the time of an orgasm. I was so embarrassed by it I couldn't look at him for days.
About a month went buy and for the first time he mentioned it to me, I immediately tried to change the subject, to no avail. He kept telling me it made his day and that he couldn't believe how nice my body is. He said he wished he could masturbate and that seeing me that night was the closest he had gotten to an erection in many years. He also mentioned how he tried everything over the years, went to 3 or 4 doctors and even tried Viagra with no effects. He would joke around with me more often than ever reminding me of the night he saw me masturbating. It went on and on and I was no longer embarrassed when he talked about it. The reason I think is because he was actually complimenting me on my figure and my success at satisfying myself. He always said he was jealous that I was able to orgasm the way I did. He kept telling me he would like to catch me again and would love to see me naked again. He was relentless with this talk for a long time and instead of me being offended by it I began enjoying the conversations we had about it.
Well over a year went by since that night he saw me and he never did stop talking about it once in a while. He brought it up again one day and asked me to let him see me naked. I thought he was joking and even asked what his brother would think. He just laughed and told me I was the only naked woman he had seen since his wife died and then said he wouldn't tell my husband. I don't know why but when he said that the two of us burst into laughter. For several weeks he kept asking to see me naked and at one time got on his knees and begged me asking me what harm it would be. To call his bluff I told him he would have to take his clothes off first never dreaming he would.
He just stood in front of me naked with his limp penis and I don't know how I got the courage but I undressed for him and let him look at me. The way he did and the way he smiled at me began to arouse me. When he asked to let him watch me masturbate I was hesitant but after a few minutes did. I couldn't believe how I felt because instead of being embarrassed it excited me just the way he was looking at me. He stood there holding and pulling on his penis but he was unable to get an erection. I must have orgasmed three times and I finally said something to him like I was sorry he couldn't get hard. He only smiled and thanked me for doing that for him and I ended up thanking him for arousing me.
We began doing this every week but after about six or seven weeks I started letting him masturbate me and now he does it all the time and I enjoy it very much never believing I could do anything like this with Dan. I do hold his penis and play with his testicles but unfortunately he is never able to get hard. I feel sorry for him but also for myself because I would have sex with him if he was able to. The funny thing is we have fun doing this and he says he likes seeing me naked but I also like seeing him naked. He only masturbates me which has become very fulfilling to me. We always joke that his wife and my husband are rolling in their graves. I truly think my husband wouldn't mind what we do. I am very satisfied but only wish Dan was able to enjoy it as much as I do. I've known Dan since I was 17 years old and never had thoughts of anything like this ever happening between us.