Answered by Shaykh Faraz Rabbani
What is the ruling on a man who has a build of prostatic fluid in his urethra? The fluid only appears after squeezing (e.g. after urinating) and does not soil his clothes. For example, prior to wudu he squeezes his penis and the fluid appears. He washes it off, does wudu and prays. After the salah he checks again via squeezing and the fluid appears again. None of his underwear is soiled. The fluid remains in the urethra until squeezed. This state lasts all day.
Your wudu would only break after the liquid actually come out of the penis. The default is that it has not come out, unless you become certain it has. You would not be considered to have a chronic excuse unless you are truly certain that the liquid has in fact come out (thereby nullifying your wudu). To be careful, it is best to renew wudu before going to pray a set of prayers. There is no need to squeeze or be excessive.