Does the discharge that comes out of the penis of someone who suffers from waswas (obsessive thoughts) after squeezing it necessitate ghusl (ritual bath) with water only, or is it necessary to repeat the squeezing until no discharge is seen?

If you see some discharge on the tip of the penis after urinating, it suffices to cleanse with water. It is not obligatory to squeeze the penis or repeat the cleansing, as that is a form of waswasah (whispering from Satan) which may cause more urine to exit. Sheikh al-Islam Ibn Taymiyyah affirmed that urine naturally ceases, and that attempting to expel it through inspection or squeezing is an innovation (bid’ah). He stated that every time something is expelled, more will come. Sheikh Ibn Uthaymeen mentioned that the cure for the delusion of something exiting is not to squeeze the penis. In case of doubt, one should not leave until he hears a sound or finds a smell, as was narrated from the Prophet, peace and blessings be upon him.