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No. Urine should be able to flow out of the penis unaided, with no physical interaction.

I would advise visiting a doctor and getting this looked at.

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15y ago
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Q: Does a boy have to squeeze his penis to let the urine out?
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How do you control urination after the removal of catheter applied for long duration?

Yes this can be a problem but you can do the exercises where you squeeze and try to cut of the urine and then let it on again. Go to the bathroom on specific hours since it is possible to get the bladder used to how often you go. You can also get help from a Urology therapist.