Self history and with a friend.
My history of masturbation.
I first discovered masturbation sitting in the bathtub where I would wash my body all over with soap. My penis would be the last part of my body to wash. I'd wash it with a thick lather of soap, especially around the frenulum, which seemed to give me the most pleasure. I remember how good it felt rubbing my dick between my two hands. This wasn't just any feeling; this was a feeling of pure bliss. So I'd sit there rubbing my dick like I was starting a fire and getting a pretty good erection going. I remember being fascinated with how big my penis got. I'd continue to rub and play with my boner until all of a sudden, I exploded with this wave of immense pleasure. I'd had my very first orgasm, though of course, back then I didn't know what it was; only that, because it felt so good, I wanted to do it again and again.
I found out much later that I could create the same feeling of pleasure by rubbing my dick between the palms of my hands, without having to use soap, or even spend time in the bath tub. From that day, I'd masturbate until dry orgasm at every opportunity, usually two to three times a day; at home in my bedroom, in the bath, or in my bed.
When I was older, I had a friend who was kind of curious, so we decided we'd play a game called 'dick-to-dick'. In this game, we'd go into a private cubicle, and pull our shorts and underpants down, until our dicks were fully exposed. The aim of this game was that the tip of the first person's dick would have to touch the tip of the other person's dick without ever losing contact. The game would be finished when one of our dicks broke contact. Whoever broke contact first would be the loser. I remember by the end of this game, our dicks would be erect pointing straight out, with the tip of my dick touching the tip of my friend's dick. I know from my perspective, it always felt so good touching the tip of my friend's dick with my own. My friend would also say 'Your one's the same as mine'. We did this several times throughout the year, asking each other at various times, 'do you want to play dick-to-dick'?, but stopped playing after that. I guess it was just natural curiosity in the end.
On my own, I masturbate in front of the mirror and at every opportunity I get. I remember, once at the age of 16, being at home one day with a wand type vibrator and lube, and using both of these to get hard. I'd keep going and going, taking turns with the vibrator and using my hand, until I had the most explosive orgasm ever, with several shots of cum piling up over me, and onto the floor.
I still masturbate two to three times per day and am not showing much sign of slowing down. I've recently bought a vibrating cock ring. I lube up my dick, and then slide the ring onto the base. At the touch of a finger, I get the best of two worlds; a miniature vibrating cock ring to pleasure the base of my penis, and the lube to work around the frenulum and tip of my dick. This technique has produced some of the most explosive orgasms I've ever had.
I'm still trying to find ways to get the most pleasure out of my dick and love reading others' experiences on this site!