Straight Male / 48
My grandmother had a neighbor who lived behind her that wore shirts way too small for her while working in the backyard and showered with the blinds open. Luckily, grandma had a small storage shed that you could watch her neighbor shower in privacy. My cousin and I knew about this and had left a pair of binoculars in the storage shed. We also didn't think grandma was aware this occurred.
I was fifteen and watching a movie with grandma. Kept checking to see if the neighbor was going to shower. When I saw the bathroom light turn on, I told grandma that I was headed out to go for a walk. To me, I was being very sneaky. In reality, it was obvious what I was doing to grandma and she was also perfectly aware what her neighbor did at night. So, I walked out the back door and headed directly to the storage shed and grabbed the binoculars.
Watched the neighbor get undressed and decided to pleasure myself. What I didn't realize is that grandma had opened the door and stepped in the shed. I was stroking away and talking to myself out loud a few dirty things. Then, I made a few sounds and blew my load into my hand. I put everything away and turned to see grandma standing there. She simply told me, nice job. I asked her if she just walked in and she said that she was there for the entire performance. I was embarrassed. This is when I found out how cool and fun grandma was.
Grandma mentioned that I should wear a comdom, so there isn't any mess. It sounded like a good idea to me, but other than buying a single condom at the gas station, I didn't have a supply.
The next day we drove to another town about 30 minutes away to do some grocery shopping. When we were done, grandma stopped at this small convenience store and heads in. She walked back out and handed me a brown paper bag. Inside were two items. The first was a Hustler magazine and the second was a box of condoms. I was shocked and realized how cool grandma was. But, it got better very quickly. Grandma started driving and she asked me if I have ever put on a condom, which I said of course. She didn't seem convinced and told me that she could show me how to put one on over a banana or a cucumber, but nothing was as good as the real thing. I will never forget what she did next. She drove about ten miles and pulled into an old rest area. There wasn't much traffic on the road and there were no cars at the place. She told me that if I got it hard, she would show me how to put on a condom. I sat in the front seat with her and began masturbating as my grandma watched. Once it was hard, she told me what to do, but I was struggling figuring it out. She took the condom and slid it over my cock and began stroking my cock. She gave me my first hand job and continued until I came.
It only got better from there. That night grandma told me she would help me while I watched the neighbor. The two of us went into the storage shed and waited for the neighbor to shower. Once the light went in, I grabbed the binoculars and grandma grabbed my cock. Once it was hard, she put on a condom and gave me a hand job. Over the next three years, grandma gave me numerous hand jobs with and without a condom. It was great. She kept this up until I was eighteen and she finally gave me the ultimate gift. I sure miss those days.
I was fifteen and watching a movie with grandma. Kept checking to see if the neighbor was going to shower. When I saw the bathroom light turn on, I told grandma that I was headed out to go for a walk. To me, I was being very sneaky. In reality, it was obvious what I was doing to grandma and she was also perfectly aware what her neighbor did at night. So, I walked out the back door and headed directly to the storage shed and grabbed the binoculars.
Watched the neighbor get undressed and decided to pleasure myself. What I didn't realize is that grandma had opened the door and stepped in the shed. I was stroking away and talking to myself out loud a few dirty things. Then, I made a few sounds and blew my load into my hand. I put everything away and turned to see grandma standing there. She simply told me, nice job. I asked her if she just walked in and she said that she was there for the entire performance. I was embarrassed. This is when I found out how cool and fun grandma was.
Grandma mentioned that I should wear a comdom, so there isn't any mess. It sounded like a good idea to me, but other than buying a single condom at the gas station, I didn't have a supply.
The next day we drove to another town about 30 minutes away to do some grocery shopping. When we were done, grandma stopped at this small convenience store and heads in. She walked back out and handed me a brown paper bag. Inside were two items. The first was a Hustler magazine and the second was a box of condoms. I was shocked and realized how cool grandma was. But, it got better very quickly. Grandma started driving and she asked me if I have ever put on a condom, which I said of course. She didn't seem convinced and told me that she could show me how to put one on over a banana or a cucumber, but nothing was as good as the real thing. I will never forget what she did next. She drove about ten miles and pulled into an old rest area. There wasn't much traffic on the road and there were no cars at the place. She told me that if I got it hard, she would show me how to put on a condom. I sat in the front seat with her and began masturbating as my grandma watched. Once it was hard, she told me what to do, but I was struggling figuring it out. She took the condom and slid it over my cock and began stroking my cock. She gave me my first hand job and continued until I came.
It only got better from there. That night grandma told me she would help me while I watched the neighbor. The two of us went into the storage shed and waited for the neighbor to shower. Once the light went in, I grabbed the binoculars and grandma grabbed my cock. Once it was hard, she put on a condom and gave me a hand job. Over the next three years, grandma gave me numerous hand jobs with and without a condom. It was great. She kept this up until I was eighteen and she finally gave me the ultimate gift. I sure miss those days.
