At what age did you ejaculate/masturbate?

[Adinnieken]

haxxiy said:

Uh, that's quite interesting. I never knew the reason why, though I've read some remembering their first ejaculation did hurt - some sort of male cherry popping, if you will.

But you're talking two different things.

There is pain with an orgasm pre-pubescence.  Likewise there is pain if you attempt to continue to masturbate after ejactulation during early puberty.  This is due to the underdevelopment of the penile tissue.

You may, or may not, have a painful ejactulation at anytime in your lifetime if you go for a period without ejactulation.  I was advised by my urologist to masturbate because of this very issue.  The volume of ejactulate and physiology can, especially when having gone unused for a period of time, lead to pain or bleeding when ejactulating.

Since the first ejactulation is the very first, this can lead to pain depending on the circumstances.

Early pubescence you'll likely feel pain on your first ejactulation as well as after if you attempt to continue to masturbate.
Later on, and post-pubsecence, you'll likely feel pain if you haven't ejactulated in a long while.  This can also lead to blood in the ejactulate or post ejaculation.  Not to be confused with pain or discharge experienced if you have a UTI or an STI.

In pubescence, the urethra is "plaiable" but inexperienced with the volume encountered with ejactulate.  A urine stream can pretty much go through any size tube.  So, the first time, yes it's possible depending on the volume and the size of the urethra that one may experience pain.  In older men, especially into the late 30's and beyond, if you have less frequent ejactulations, the urethra becomes less pliable and combined with the volume of ejactulate can lead to pain and or bleeding. 

My apologies if this goes into far more detail than you or anyone else wanted to know.  I'm an explainer.