Summer before sixth grade for me - climbing a pole at the school playground. Humping it really. I had discovered a few years earlier that a stationary climb tickled in a good way. Sticky mess but started masturbating like crazy then on.

do girls count? i was 18 in the navy and polishing my boot (which was between my legs) - spit shinning it - spit then rub in a circular motion to shine it - suddenly my face was red - i wasn't sure what was happening and then the waves - the overwhelming waves - wow - after that i had the shiniest boots in the Navy.

Oh my gosh.... I wanna come back as a boot.

Thank you Kansas!

In my profile I said I wanted to come back as a woman's bicycle Seat. Thanks to that story, I need to make a revision.

My first time was very similar except I had stumbled onto jerking off long before I could cum. One night I was lying on my back in bed and suddenly my balls clinched up. I shot a hot sticky stream all the way up to my forehead! It felt great but because I had never cum before I was also terrified.

Once I figured out what had happened, I discovered my new favorite hobby. The only thing better than playing with my dick was getting my downstairs neighbor to do it for me. Her hands were softer and she seemed to enjoy it asmuch as I did.