During the last 23 years, I have had many jacking experiences with others. This story is about the first time, when I was 18 years old.
It was right after graduating from high school in 1987. Steve and I were friends throughout junior high and high school and graduated together. After graduation, we were both going to go to the local community college, so we remained good friends and spent a lot of time together during the summer. One of the great things about having Steve as a friend was that his dad owned a local convenience store. That gave us access to two thing we both enjoyed, beer and porn magazines.
Steve worked every Friday night at the store store with his older brother. His brother worked at the register because he was over 21, and Steve did general stocking and clean up in the storage room. During his shift, he would grab some beer for us to drink the following night, along with the latest editions of Playboy and Penthouse. The brother and dad worked Saturday nights, so Steve and I would always get together to hang out. Sometimes we would park in a vacant parking lot near my house where we would have lots of privacy. We would talk about the usual stuff that guys talk about, like work, girls, sports, etc. We would also look at pictures in the magazines and talk about what we liked about each of the models. We did this every two or three weeks for the first two months. Then one night, things changed. We were sitting in Steve's car, having some beer and looking at magazines, when we both started squirming. My cock was completely hard and was uncomfortable in my pants; Steve was feeling the same way, and I noticed him grab his bulge and shift his cock around. Seeing him do this made me think it was okay if I did the same thing, so I grabbed my cock and shifted it until I felt better.
Even though Steve and I had seen each other naked in the gym locker room and showers at school many times, we had never seen each others cocks while they were hard. When we had looked at porn magazines together, we both knew we each had hardons, but never considered taking them out of our pants or anything like that. After our porn magazine sessions, I always went home and jacked off, and I assumed Steve did the same. On this night though, he surprised me. After we each shifted our cocks in our pants, he said 'the pictures are really getting me worked up tonight, I really need to jerk off'. Even though this caught me off guard, I was able to quickly reply, 'don't let me stop you, I feel the same way'. That was all it took, immediately Steve undid his pants and slid them down to his ankles while his cock popped straight up; as soon as I saw him do this I followed and did the same. It felt great to release my cock from the confined space in my pants. We each grabbed our own cock and started stroking while still looking at the pictures in the magazines and talking about the models. The feeling of stroking my cock in front of another person while discussing the tits, pussies, and bodies of the beautiful women in the pictures was incredible. Neither of us lasted long and after just a few minutes we both came all over ourselves; after cleaning up we went right back to having general discussions, as if the jackoff session never occurred.
Over the next year or so, Steve and I jacked off together many times in similar and completely different situations. I will follow up with stories about some of the different ones soon.