I hope this doesn't offend anyone. It really happened last year.
Last year I was visiting my Grandma. She has been a widow for many years. She was 72 then and she is still spry and active for her age. As is so often true, many times Grandparents and granchildren develop a very close bond, sometimes closer than parents and their own children.
She has always been very upfront with me in her use of language and she never holds back. She asked me how my dating life was and if I was 'getting any' lately. That's my Grandma for you! I told her that it had been a pretty long time. Being open with her as she is with me I told her that my hand had been my best friend lately. She just laughed and said she could understand that. She said 'Elmer (my deceased Grandpa) was always playing with his.'
'So how often do you do that?' she asked me. I told her I did it about twice a week. I can't explain it, but for some reason I could feel things hardening in my pants as my Grandma and I talked about this. There was a sudden immediate feeling I was experiencing that was both confusing me but also exciting me at the same time. I was truly getting a hard-on! In front of my GRANDMA of all people! My mind was having thoughts of sitting naked in front of my Grandma and jacking off as she watched me. I couldn't get these thoughts out of my head and I kept getting harder and harder.
I gathered my courage and I said 'Gramma ... I can't explain this ... but I'd really like to jack myself off right now. Would you watch me?'
My heart was racing. This was soooo wrong the other half of my brain was telling me. The instant I got those words out of my mouth I regretted saying them but it was too late. She just gave me a nice smile and said 'if you'd like to jack yourself off, yes, I'll watch you.'
I couldn't believe it. What in hell was I doing? I was so darn hard. My Grandma watched me as I stood up and took my pants off, then I slowly pulled my boxers down and off my feet. My Grandma looked at my dick and then looked me in the eyes and said 'you have a very nice dick!'
I sat down beside my Grandma and took my dick in my right hand and I started slowly jacking myself. I told her that I did this several times a week and how I loved the feeling, and I told her that it was exciting to me having her watch me. She even reached over and felt me and gave me a few strokes. I continued jacking off until I shot my cum all over my stomach.
When I finished she asked me if I felt better having given myself some relief, and I told her I felt great! I don't think my Grandma minded watching me at all. I never did this again with her though.