I have a lot of problems making sure that no urine remains in my urethra after urination. It takes me about 10 minutes to press between my penis and anus and then press up to the point of circumcision three times – istibra. However, every time I repeat this process, more urine is emitted. Is this common?

To apply pressure three times only takes three seconds – the time to complete the process.
The maximum time needed for istibra is less than 20 seconds, and there is no need to perform it again. The main point about istibra is to ensure that no urine is left in the urethra.