I am 57 and I have a good lady friend in her early 60s. We have lived a few houses apart for about twenty years...
We have had many conversations. Her husband passed away four years ago, and my wife up and left me last spring. This elegant lady makes a living giving art lessons and teaching part-time at the local college.
A few weeks ago, in the early autumn, we raked leaves together and later sat down to tea and my homemade cookies. The conversation turned to her art. She asked if I would be willing to pose nude for her, so that she might sketch me. I told her that I had never done this before, and might feel especially self-conscious naked around her as we had been friends for so long. She said that she would like me to try, and if I felt uncomfortable then I could simply get dressed and we would stop.
She led me into her sunroom studio, and drew the sheer curtains closed. Although it was later in the afternoon the room was still warm. She asked me to undress and sit on a padded wooden stool facing a certain plant in the window. She left the room while I undressed, and when she returned I was already in position facing away from her.
I heard her pull out her chair behind her desk and arrange her materials, then she asked me to adjust the position of one arm, then raise my chin slightly, rotate a bit clockwise, etc. We did not speak and I could hear her sketching away behind me.
After a few minutes she asked for several other changes in pose and I did as she asked. Her sketching sounds ensued, and after a few more minutes she asked me to stand, turn to face her, and put one foot on the lower level of the stool.
This placed my flaccid cock and my hairy ballsack fully in her view. I was surprised to see that she was sitting naked at her desk, her large nipples and ample breasts in full view. She returned to her sketching for a few minutes, then she moved her chair back, rose, and began walking toward me.
With her left hand she was fingering herself, while her right hand cupped her left breast, massaging the nipple. She said that she wanted very much to masturbate right now, laughing as she said it. I told her that I would like to masturbate with her too, and as she approached me I felt myself begin to harden.
As she passed, she grasped my member and gave it a squeeze and a few strokes. We moved over to sit on her couch and she spread her legs open and started rubbing her clitoris and sliding her fingers inside herself. I grasped my cock and began jacking myself, I told her how much it was turning me on to be naked and masturbating in front of her.
She smiled and said she wanted to see me cum. My erection was quite hard by now, throbbing in time with my heartbeats. I was really quite aroused. I told her how good it felt, and she told me how exciting it was to watch me.
I told her when I was close to cumming. She began to concentrate on frantically rubbing her clit, this aroused me even more, and suddenly I squirted cum all over my hairy stomach. My stroking slowed, but for eight or nine strokes cum flowed out of my pee-hole.
Her fingers frantically worked at her 'little man in a boat' while her other hand tugged at her breast. She came within two minutes. We smiled and relaxed for a moment, then she grabbed a handful of tissues and began to clean me up.
She peered intently at the head of my penis, then grasped the shaft, and with her finger she wiped away the last drop of cum that emerged from my limp member. Then we got dressed, making plans to go out for a meal. There is more to this story, but I shall relate subsequent events at a later time...