My best friend was 12 and I was 11. He could shoot and I hadn't ejaculated yet. I had only humped the floor or pillows and had dry orgasms. My friend kept talking about "squirting" and he taught me how to jack off. I was amazed to see him cum while my orgasms were still dry, but not long after I started shooting too.

I was 13, he was much older. Best experience ever and never regretted it!

i dated an aussie girl years ago - pure filth!on second date she told me were were going back to hers and that i would be jerking my cock for her while she watched!
She stripped and gave me instructions while she watched - knelt in frotn of me and told me to cover her tits! i was 19 she was 28!

I almost got caught like that once when then GF and I were both 15. We'd got naked round hers one afternoon and were having some fun when her sister who was a year younger came home unexpectedly. We'd both managed to get our jeans back on but little sis opened the door to find us both topless (GF was a big girl for her age) then closed it quickly. Expected the worst as they were a church family but nothing was said.

Was an older cousin who dared me to jerk it when I was staying over one night.

Wanking with 2 neighbour boys to dry orgasms at very young age. Standing in the nature.

Keep the stories cumming

I was 11 and playing naked with my same aged next door neighbor. We would often hang out naked and play with our cocks. One day we were just stroking when we both had our first orgasms and began shooting our loads of cum. We did a good job of covering each other with fresh warm sperm. We licked it all up and continued to jack off and suck each other for many years.

Some great first times here

I always wanted to jerk in front of a girl when I first started dating but it was at an age where it wasn't "cool" to jerk off (even though everyone knew everyone else did too) so I never mustered the courage until I was in my early 20's.

The very first time doesn't really count as far as I am concerned. I went to a massage parlour and after she gave me the rubdown, she told me if there was anywhere I wanted her to massage, to show her by massaging it myself. I knew immediately that this was to prove that I was not a cop, so I jerked my cock a few seconds until she said okay and then took over.

But the very first time I did it to completion was one of two times, I don't remember which came before the other so I will share the details of both:

I saw an advertisement for a "Lingerie Show." It was at the back of a porn shop and the sole girl there explained how it worked: she would change into some lingerie for my viewing pleasure. I had the option to masturbate or for some extra $$$, she could tug me herself.
I hadn't brought enough cash for the helping hand and this was at a time when ATMs weren't so easy to find, so I was more than happy to stroke my cock to my own private model.

The other time that may have been my first was a place that advertised as massage but also offered a "Self Massage" option. You paid an entrance fee (I think it was $25 or so) and then a girl watched you jerk off. For every minute it took you to finish, it was an extra $2 per.
Good gig for the girl, she doesn't have to do anything but watch, the quick guys can get out quickly for the next client and the guys with stamina pay pay her most.
I thought it was a great business model and it should be more commonplace but I've never seen another.

Sadly most of these jack-shacks have long disappeared, replaced by far more expensive massage parlours.

In front of my wife after she had caught me jacking a week before. In an argument over that she said if you like that so much why don't you do it now....I did and she just sat there red faced and stunned into silence....best load in a long time....
Since then I have been on several cam sites dropping loads and some in the flesh shows for a female peeker