I have been jerking off for as long as I can remember. But early on I guess it was just playing with my self.
Once I found that wonderful feeling by rubbing the underside of the head of my cock I have not stopped. I was always out in the neighborhood looking for secret places to wack off. Some not so smart considering I could have been caught. The first one that pops into my mind was on the back steps of a church building. It was obscured by a giant pine tree. But it was the middle of a hot summer day and I could have been found. I always wore really short running shorts. I would just reach my hand up the leg and pull my cock out. It would always be so hard with the veins just pulsing. But the swollen tip was so smooth and taut. I sat there on the top step with my legs spread and one short leg pulled up in my ass crack. Which also added to the pleasure. I sat there at first slowly stroking it and staring at it. Then I would just start pounding it in my fist until I shot huge amounts of thick white cum all over the steps.
Another place I liked to jerk off was under a highway overpass. I would only do this late at night though. I would take walks after midnight in the summer that always led to the highway. I would climb under the bridge and stand up at the top of the embankment where the girders connected. There wasn't a lot of traffic but it would get me so hard to be jacking off as cars would drive by as I played with myself. During these times I would take my time and slowly work my cock until I shot all over the ground and the girder.
Another thing I still like to do is play with the shower massage. There is a setting that makes a spary only from the center of the head. This is the closest I can get to the sensation I used to have when an ex girlfriend would suck me off while scratching under my balls with her finger nails. Sometimes I will just let that spray hit me there until my cock is so hard it starts to drip. Then I wack it off like crazy shooting my cum all over my chest.
I would also have this same girl chew on the area just under my balls while I jerked off. She seemed to really love it when I asked her do that. At the same time she would have her hand between her legs working her clit and fucking herself. Sometimes I wouldn't even fuck her. We would just use each other's bodies to masturbate. I liked to oil up her perfectly round small ass and just slide my cock up and down her tan lined ass crack until I left a pool of cum on the small of her back. She would some times just mount my face but didn't want me to lick her. She would just rub her pussy and clit all over my face. She would end up fucking my chin most of the time. And when we did fuck she always had her hand between us working her clit as I slid my cock in and out of her.