This is a true story. It's long but worth it.
I am a 29-year-old male. I do think that I am an attractive guy, and I do have women often telling me this. Although I have only slept with approx. 20 women, I have been extremely lucky with the sexual experiences I have had, actually, there's not much I haven't done.
Lately, I have been getting bored. I have found that having a partner watch me jerk off has been really exciting. I occasionally take a stroll through the local mall. There is one store in particular that sells woodwork, shelves, beds etc. I have noticed this older blonde woman working in there. I have been in the store a few times and we are on a friendly hello type basis. She is about forty to forty-five-yrs-old. Natural blonde, tanned, about 5'4, probably just over 100 lbs. I have noticed that she loves to wear leather pants. She has a black and red pair. I am a confident forward guy, so I had a plan in mind. I had noticed that there is a room in the back where some of the smaller stock is stored. So, after working up some courage, I went in and said 'Hi there, I just want you to know that I have seen you before, I've walked by many times and I think you are absolutely beautiful.
She was very flattered. By the way there is no ring on her finger. I then proceeded to tell her how hot and sexy she looked in her tight black leather pants. She was very thankful. I could feel my hard on starting to rise so I said 'See you soon!' I went to get a coffee and then decided to go back. I walked in, she was surprised to see me again. I sat down at the little desk set up for clients to do paperwork on. She looked at me strangely and said 'Are you buying something?' I said 'No, I have something to ask you.' She looked at me strange. I said to her that what I am about to ask might offend her and if it does I will leave and not return. So she said what is it? I said 'I noticed you have a private room back there. I said that I would be forever grateful if I showed up with her a half hour early tomorrow, we both go in the back room and have her watch me jerk myself off.
Her eyes bulged open. She started laughing and so did I. She said are you serious, I said yeah. She said, this is a first for me. I said it was a first for me too. I told her how sexy she was and it would be so hot for me. She smiled and said ok. She said she didn't work for two more days, so we agreed for it to happen on Thursday morning, I asked her to wear her leather. I didn't jerk off again till that day. I showed up a half hour before opening at 9:30am, and she was already there. She looked totally hot.
We opened up and went in to the back room. There was a chair in the back room and she grabbed another from the front. I took off my clothes and exposed my stiff six inch hard-on. She was excited to see it and told me it looked nice and she also told me how sexy I was. I got out my lube of choice and nervously started to stroke myself. I had also armed myself with tons of tissue. She told me how excited she was about it. She encouraged me to shoot a large load. Before long, I could feel what I knew was coming.
Suddenly I started to shoot, there were at least four or five long thick ropes of cum that went splat on the floor. She was moaning and she said that it looked really hot. We continued to do this about once a week, eventually I started to cum on her tits. This went on for a couple of months, and then she regretfully informed me that she had got a higher paying job, I haven't seen her since. Word of advice guys, there's not many women who don't like to watch a man jerk himself off.