So this all happened a while ago. I had this older neighbor who was a lot older than me. I knew him for a while until we moved away, but something happened before we moved.
They had a those circle pools in their backyard the ones you have to buy (it didn’t come with the house) and I remember he used to sit on this chair and lay there in the sun when it was warm out. They often used the pool and I remember I made a habit of watching them because his wife would often wear a swimsuit and that’s pretty much the only time I’ve seen her with less clothes on. Same with their daughter who is my age. I know it’s pretty creepy to admit but it comes up later.
One of these days that I was kinda looking at their backyard. I noticed my neighbor sitting there with a magazine in hand. I checked again periodically and that’s all he’d do. One of these times I saw him jerking off, again I know it’s weird to admit this but it comes up later. I’ve never really seen anyone nude at the time so it was kinda interesting. He would do this a lot and he would bring porno magazines (I found out that’s what they were later.) Anyway, I caught him doing this a lot but didn’t say anything. One of these days I was home alone and I caught him, I guess I was moving too much because he saw me watch him even with the sun in his eyes somehow? I’m not too sure but yeah he caught me. He came to the door and apologized a lot and I said I didn’t mind it, I was just curious on what he was doing. He promised to never do it again and I told him it was fine. He ended up not doing it at all for the next year or so.
About a year later, I was at their house for his wife’s birthday and I was on their backyard alone pretty much. Til I saw him come out and it was kinda awkward at first. He asked me how college was and stuff of that nature, then he moved on to me spying and asked if I still did it. I told him not as much, and he asked if I enjoyed the view of his wife, he assured me he wouldn’t be mad if I did he just wanted to know. I admitted yes and he was like cool. I apologized to him about the spying and he said it was fine, it’s something he would’ve done at my age, and he apologized again for what he did. I told him it was cool but I was wondering why he always held a magazine. He ended up explaining what a porno magazine was and we went in his basement and he showed me a few and offered to give me some. I accepted one and I took that home. Later that week, I gave it back and we were really good friends pretty much. We talked about a lot of things, and he knew pretty much everything in my life. I’ll skip over that since this is a jerk buddy story. Anyways, we were in his basement and he asked if I had ever had sex before and I told him I didn’t. We talked about my school crush and he offered to help and give advice and stuff. He asked if I ever jerked off to her and I admitted I did. He paused and asked if I ever jerked to his daughter and wife and I told him to not be mad but I did. He laughed about it and told me it was pretty hot that I did.
We bonded a lot through that summer. I remember he would let me know when they were going to use the pool and I would be ready. He would always remark that I was probably jerking off at the window and I told him I was.
One of these days, near the time I had to move away, he offered to show me his wife’s nudes and I gladly accepted. We were in his basement just watching videos he took just for me to see of her. I got to see her big boobs and it was really hot. He told me I could jerk off if I wanted to, and he would leave the room so I could enjoy. I asked if he was sure and he said yes. He left the room while I jerked off and the computer screen saver thing kicked in and I had to put the password and I asked him to come back in and he came. I covered my cock and he put the password. He offered to jerk off with me if I was cool with it. I told him I wasn’t gay and he told me it wasn’t, we’re just two guys jerking off to his hot wife. I saw his point and agreed. He buckled his belt and pulls down his pants. He was already semi hard and told me nothing you haven’t seen before. and I stopped covered my cock (which immediately poked up) and he said I had a young hard cock. My cock was a little bigger than his, but his was hairier. We were both jerking off side by side, he ended up getting naked and he had a big gut I have to admit. He showed me some of the porno magazines and I showed him my crush and some porn I jerked off to. Porn like cartoon porn, video game girls or actual porn stars I liked. He ended up cumming first and when it was my turn he offered to jerk me off. I said yes and I started moaning my crush and he put the photo I showed him earlier on and I ended up cumming to her. Overall it was an amazing time, I live a little too far since I don’t have a car to do it again, but I’d would like to.
so if anyone out there wants to chat about this id be down!