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I started to masturbate a few months ago, but haven't really felt good until now. But when it does feel good it doesn't feel good for very long, in fact it tends to hurt after a while. The only time it has felt good is when I have used the shower head. Can anyone tell me why it doesn't feel that good?
You may not have conditioned your head for such friction yet.
If you are not circumsized, your glans (head of the penis) may still be very sensitive, and too intense stimulation may almost be painful.

Or, are you saying the ejaculation is painful?

The shower head may be a bit more gentle or less intense, and more easily controlled by you. Perhaps that's why.

But really, only you can tell what feels good, and what's too much.

You may find that less frequent sessions will make it feel better, too.
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