Sorry I haven't written any new stories lately. I have many more to share with all of you if you like them. Shoot me an email and let me know.
In high school I used to cut grass around my neighborhood for extra money. It was physical work which kept me in shape and I got a great tan. One yard I used to love to cut was a house that had a tall wooden privacy fence around the back yard. I always felt pretty comfortable there because one of my parent's friends lived there and they were pretty cool people. The guy was a teacher at our school and also coached the soccer team. He was probably around 25 to 30 and his wife was hot as hell. It was pretty sunny and secluded back there so I would often imagine myself sliding my shorts off and jacking off while I was there. It was a pretty risky thing to do and I never tried it until one day in August when I was super horny. While I was cutting this particular day, I noticed how hard it was to see behind these bushes and trees off to the one side of the yard. I just kept thinking how it would be pretty easy to strip naked there and jack off. I hadn't ever done anything like that so it was both a thrill and pretty dangerous. I decided to just go for it so I turned off the mower and slid back behind the bushes where I thought I was completely covered. I slid off my shorts and eventually stepped out of them and began to jack my 16 year old dick off slowly at first. I was so turned on by doing it outside that I almost came right away. I think it only took about 2 or 3 minutes until I shot a huge load on the side of the fence. After I was SO worried about getting caught I got dressed and just finished the yard and left. The next week when I got to this house again I couldn't stop thinking about how I had jacked off the week before while there. I guess at that age my dick ruled my brain. I waited until I was finished and slid behind the bushes again and stripped naked and jacked off again pretty fast. The thrill of potentially getting caught definitely made my orgasm pretty intense. Each time I did it afterwards I would feel completely weirded out by what I had done and vowed not to do it again. But I kept at it. Each week it was the same, I would cut the grass and then slide back behind the bushes and do it again. One Saturday in late September I noticed that Mr. McConnell (he was the teacher that lived there) was in the garage working on his car. I thought that I shouldn't do my usual jack off in the bushes this time because I didn't want to get caught. As I got closer to finishing the back I just got hornier and hornier thinking of risking jacking off with Mr. McConnell so close by. I knew I shouldn't try it, but my dick once again won and I found myself behind the bushes again. About a minute into it I heard a crunch of leaves nearby and froze. I started to look around through the bushes and didn't see anything at first. All the sudden, I saw Mr. McConnell walk within 10 feet of me. I just about shit myself right there. I just kept still as possible. He turned around and was looking around the yard and calling my name. A normal person would have grabbed his shorts and pulled them on but I was SO turned on at that moment I just stayed where I was and kept rubbing my dick. About 30 seconds later I shot the biggest load ever from jerking off! Thank god he didn't see me or hear my heavy breathing. I got my shorts on and waited until he walked by the back off the garage and then jumped over the fence and walked around the other way and acted like I had been in the front yard the whole time. Mr. McConnell looked at me kind of funny like he knew what I had been doing. Even though I was pretty sure he hadn't seen me it felt like he had. The next week when I got there Mr. McConnell was in the garage again and he waved to me and said he wanted to talk to me. I was pretty nervous waiting to see what he was going to say. All he wanted to talk about was paying me extra for leaf clean up in October. I thought for sure he had seen me and was going to fire me and tell my parents. We walked around the yard and he showed me everywhere that he wanted the leaves cleared out. When we got to the back yard and near the bushes he was showing me that area and said without blinking that make sure you rake behind the bushes so when you sneak back there you aren't crunching the leaves. I looked at him like huh? He grinned at me and said yea Nick I have seen you go back there several times. He pointed up at the house and pointed out a window right behind the bushes and pretty high up. If someone was standing at that window they would be able to see right down behind the bushes. I literally died of embarrassment at that moment. I started apologizing and told him I wouldn't do it again etc. He just looked at me and started to laugh. Next thing I knew he was telling me that he enjoyed watching me and to please do it whenever I wanted. Now I was totally freaked out. I just bluntly asked him if he was gay and he said not at all, but he said watching someone like me that was young and good looking and naked it was a turn on. So I said ok but I doubted I would do it again. Just like that he said that was fine and he left and went inside. I cut the lawn and started working on the leaves and kept thinking about how he had seen me from the window and watched me jack off. I was even more turned on. Not by him but by the whole situation. I knew I was going to do it again. I actually stopped right then and walked behind the bushes and acted like I was alone when I knew he was probably watching. As I stripped and got hard I had to look up at the window and sure enough I could see him there. I decided to look right at him and stroke my dick. I came like a fucking geyser. When I was finished he actually waved to me and then disappeared. Mr. McConnell never said anything to me about it again, but he would always watch me most weekends. I cut their grass the rest of that fall, but then they moved pretty far away for me to cut their new house. When I would see him around school he would always wink at me but never said anything about my showing off again.