Many years ago in my early 30s I worked for a company and dealt with a female sales executive. She was about 15-20 years older than I was and really on top of her game. Kay was pretty not beautiful, dressed very well, and was extremely intelligent. We did a lot of business, had a few lunches together and generally had a great business relationship.
When I left that job we kept in touch and networked over the years and became friends. Kay has long been retired and just celebrated her 78th birthday. Her husband passed a few years prior and she was living alone and enjoying life. Recently my job brought me to the city where Kay lived and I decided to give her call to say hello. We talked for a while and I asked if she would like to get something to eat together but our schedules conflicted. In the end she asked me where I was staying, and she suggested she drop by later that evening we could meet in the bar have a drink and catch up on old times.
I went down to the bar had a beer and about an hour later Kay showed up. We talked for about an hour and she said she had to go. As she was walking thought the lobby she commented this is a great old hotel and she had heard they have redone all the rooms and they were fantastic. I agreed, then Kay asked me if I would mind showing it to her (This would have a different meaning later.) We went up to the room a JR Suite and she looked around and said this is really nice. She sat on the sofa and said sit down lets talk. We talked for a few minutes then she said when are you going to masturbate tonight. I was in the state of shock. She laughed and said all men who travel do the same thing. Work all day, have dinner, maybe have a drink or two, go back to your room masturbate, go to bed, then start over the next day. I agreed not far from the truth. So she said you have had dinner and drinks so you know whats next. I was a little confused as to what she wanted, and didn't know what to do.
Kay then went on to explain that she and her husband had a good sex life but sometimes she really wasn't into it after a hard days work, and an evening taking car of kids. So as she got older she would tell her husband if he needed to come it was OK but she really wasn't up for sex that night. She then suggested he undress for bed and masturbate, and she would watch and encourage him. Before he died it was about 50/50 intercourse vs masturbation. Kay then went on to say when a man has the urge to ejaculate he should because delaying it leads to sexual tension and destructive behavior (smart woman).
Kay then went on to say she really learned to enjoy watching her husband masturbate, and admitted sometimes she said she wasn't in the mood just so she could watch. She went on to say she has not seen an erect penis since her husband passed and really missed it. So if you are going to masturbate tonight it would be a great favor to me if I could just sit here and watch. At that point I didn't know what to say, I said I need to use the restroom I will be right back. In the bathroom I noticed there was one of those white terry cloth robes better hotels give there guests to use. I figured what the heck undressed, put on the robe and went back to the seating area. When I came out Kay smiled and said thank you for understanding her needs, and I said I am glad happy birthday. Then I said how do you want to do this? She said just take off the robe and stand a few feet in front of her and get to work. I couldn't believe it there I was stark naked masturbating three feet away from her face. I didn't take long before I was erect and ready. She commented that I had a good looking penis and noticed that I shaved the penal shaft and my balls but left the rest off the pubic hair alone. She said it looks like about a six incher I said about six and a half. She commented yes about the same as my husband but a little thicker. Kay took out her cell phone and said do you mind if I take a close up picture of your penis to remember you by. At this point the penis talk and stroking were too much and I exploded, cum all over the place. Kay said got it, she had taken a photo just at the time I came, great shot she said.
She then said thank you for a lovely evening and suggested I put on the robe and show her to the door. As we got to the door she said when I am in town again I should give her a call. Then kissed me on the cheek and said thanks for the photo she will keep it in a safe place and look at it often.