I am 32 and I have a live in girlfriend. Across the street we have a married couple in their early 40's. We are friends and do a lot of things together. My girlfriend and the woman across the street are quite open about discussing things and joking about sex in front of us guys. One time when we were all together the topic of masturbation came up and the girls were joking about how guys did it all the time (as if they don't too?) In front of everyone I said 'Hell yes, I do it and I love doing it!'
About three weeks later I was home in the middle of the day working from my home office. I went to get the mail and my neighbor across the street was getting hers. We talked for a while. While talking she got a sneeky look in her eyes and said 'so you like to choke the chicken, huh?' I laughed and said 'whenever I can!' and she laughed.
She looked at me and said 'how about right now?' I asked if she was kidding and she said no. I said 'REALLY? You want to watch me jack off?' She said she would love to as long as I never told my girlfriend or her husband. I said 'do you think I'm crazy? I'd NEVER tell anyone!' I said 'your house or mine!'
She said to come on in to her house. Wow, I was hard before I even got in the front door! She admitted a fascination with male masturbation and ever since I had mentioned it she said she had thought about it. I was kind of nervous standing there with my big boner in my pants. I asked her if she wanted me to sit or stand or what? She asked me to sit in a chair. She walked up to me and hugged me and squeezed my dick and told me how badly she wanted to see it and how badly she wanted to watch me.
I took my pants off leaving my t-shirt on and sprawled in her chair. My dick was throbbing hard. She got down on her knees in front of me and looked at it and felt it and gave it some strokes, and made some very nice comments about it. I asked her if she would get naked too but she smiled and said no, not this time but maybe another time. OK with me!
I stroked and jacked myself as she kneeled there watching and talking to me in a naughty way, like 'I want to see you squirt that cum...come on baby, squirt your cum for me.'
It felt so hot doing this in front of a totally clothed woman, although I would rather she had been naked. I leaned back in the chair, pulled my t-shirt up, and squirted my goo all over my stomach. The whole time she was saying 'Yeah, baby! yeah!! Cum for me!'
Afterwards she said I sure had a nice dick. I told her I loved showing it to her. We agreed again to not say anything to her husband or my girlfriend, and of course we wouldn't dare!
We talked again several weeks later and she admitted she had had her period the day I jacked off for her. I told her that meant she was NOT having it now! I asked her if we could do it again with her participating and she said OK! Hooray! We went inside her house and we both got naked and watched each other. What a nice body she has! She has a 'to die for pussy' and small but firm breasts and perfect brown nipples. It was wonderful being naked and hard and openly jacking in front of her as she worked her clit for me. We each had huge orgasms.
We have this little masturbation secret now and we have done this several more times. We know it is extremely safe from a health risk standpoint and the way we arrange the times we feel confident we won't be discovered.